- Structural Revision of the Ring-Opened Product in the ZnCl 2-Catalyzed Reactions of 1-Benzyl-2-phenylaziridine with Thiols
-
The reported β-amino sulfide structures for the products in the ZnCl2-catalyzed ring-opening reactions of 1-benzyl-2-phenylaziridine with thiols should be revised to 2-amino-1-phenyl-ethyl sulfides from 2-amino-2-phenylethyl sulfides.
- Furuta, Yukiko,Kumamoto, Takuya,Ishikawa, Tsutomu
-
-
Read Online
- Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride
-
A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.
- Chiba, Shunsuke,Pang, Jia Hao,Takita, Ryo,Wang, Bin,Watanabe, Kohei
-
-
- Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines
-
Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.
- Kakiuchi, Fumitoshi,Kochi, Takuya,Morimoto, Yoshihiko
-
p. 13143 - 13152
(2021/09/28)
-
- Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis
-
The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.
- Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal
-
p. 3943 - 3957
(2021/04/12)
-
- Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor
-
Despite the fact that continuous flow processing exhibits well-established technical advances, aqueous micellar chemistry, a field that has proven extremely useful in shifting organic synthesis to sustainable water-based media, has mostly been explored under conventional batch-based conditions. This is particularly because of the fact that the reliable handling of slurries and suspensions in flow has been considered as a significant technical challenge. Herein, we demonstrate that the strategic application of an oscillatory plug flow reactor enables heterogeneous catalytic reductive aminations in aqueous micellar media enhancing mass transport and facilitating process simplicity, stability and scalability. The micellar flow process enabled a broad range of substrates, including amino acid derivatives, to be successfully transformed under reasonably mild conditions utilizing only very low amounts of Pd/C as a readily available heterogeneous catalyst. The preparative capabilities of the process along with the recyclability of the heterogenous catalyst and the aqueous reaction media were also demonstrated. This journal is
- ?tv?s, Sándor B.,Buchholcz, Balázs,Darvas, Ferenc,Kappe, C. Oliver,Novák, Zoltán,Sipos, Gellért,Wernik, Michaela
-
supporting information
p. 5625 - 5632
(2021/08/16)
-
- Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D
-
N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.
- Mock, Elliot D.,Kotsogianni, Ioli,Driever, Wouter P. F.,Fonseca, Carmen S.,Vooijs, Jelle M.,Den Dulk, Hans,Van Boeckel, Constant A. A.,Van Der Stelt, Mario
-
p. 481 - 515
(2021/02/05)
-
- Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
-
A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
- Airoldi, Veronica,Piccolo, Oreste,Roda, Gabriella,Appiani, Rebecca,Bavo, Francesco,Tassini, Riccardo,Paganelli, Stefano,Arnoldi, Sebastiano,Pallavicini, Marco,Bolchi, Cristiano
-
supporting information
p. 162 - 168
(2019/12/11)
-
- CATALYTIC SYSTEMS FOR STEREOSELECTIVE SYNTHESIS OF CHIRAL AMINES BY ENANTIODIVERGENT RADICAL C-H AMINATION
-
In one aspect, the disclosure relates to a mode of asymmetric induction in radical processes based on sequential combination of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution. Also disclosed is an asymmetric system for stereoselective synthesis of strained 5-membered cyclic sulfamides via radical 1,5-C—H amination of sulfamoyl azides. The disclosed metalloradical system can control the degree and sense of asymmetric induction in the catalytic radical C—H amination in a systematic manner. The disclosed system is applicable to a broad scope of substrates with different types of C(sp3)-H bonds and exhibits reactivity and selectivity, providing access to both enantiomers of useful 5-membered cyclic sulfamides in a highly enantioenriched form. Also disclosed are catalysts useful in these processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
- -
-
Paragraph 0201; 0242; 0244-0245; 0248-0249
(2020/11/27)
-
- Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage
-
Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.
- Zhang, Jianbo,Chang, Sukbok
-
p. 12585 - 12590
(2020/08/21)
-
- Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
-
A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
- Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
-
supporting information
p. 3853 - 3857
(2020/07/27)
-
- Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations
-
Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.
- Louka, Anastasia,Kidonakis, Marios,Saridakis, Iakovos,Zantioti-Chatzouda, Elisavet-Maria,Stratakis, Manolis
-
p. 3508 - 3514
(2020/06/02)
-
- Ruthenium(II) Complexes of Heteroditopic N-Heterocyclic Carbene Ligands: Efficient Catalysts for C-N Bond Formation via a Hydrogen-Borrowing Strategy under Solvent-Free Conditions
-
Both imidazol-2-ylidene (ImNHC) and 1,2,3-triazol-5-ylidene (tzNHC) have evolved to be elite groups of N-heterocyclic carbene (NHC) ligands for homogeneous catalysis. To develop efficient ruthenium(II)-based catalysts incorporating these ligands for C-N bond-forming reactions via hydrogen-borrowing methodology, we utilized chelating ligands integrated with ImNHC and mesoionic tzNHC donors connected via a CH2 spacer with a diverse triazole backbone. The synthesized ruthenium(II) complexes 3 are found to be highly efficient for C-N bond formation across a wide range of primary amine and alcohol substrates under solvent-free conditions, and among all of the complexes studied here, catalyst 3a with a mesityl substituent displayed maximum activity. To our delight, catalyst 3a is also effective for the selective mono-N-methylation of various anilines utilizing methanol as a coupling partner, known to be relatively more difficult than other alcohols. Furthermore, complex 3a also delivers various substituted quinolines successfully via the reaction of 2-aminobenzyl alcohol with several secondary alcohols. Importantly, catalyst 3a exhibited the highest activity among the reported ruthenium(II) complexes for both the N-benzylation of aniline [achieving a turnover number (TON) of 50000] and the realization of quinoline 8a by reacting 2-aminobenzyl alcohol with 2-phenylethanol (attaining a TON of 30000).
- Donthireddy,Mathoor Illam, Praseetha,Rit, Arnab
-
supporting information
p. 1835 - 1847
(2020/01/31)
-
- Scalable preparation of stable and reusable silica supported palladium nanoparticles as catalysts for N-alkylation of amines with alcohols
-
The development of nanoparticles-based heterogeneous catalysts continues to be of scientific and industrial interest for the advancement of sustainable chemical processes. Notably, up-scaling the production of catalysts to sustain unique structural features, activities and selectivities is highly important and remains challenging. Herein, we report the expedient synthesis of Pd-nanoparticles as amination catalysts by the reduction of simple palladium salt on commercial silica using molecular hydrogen. The resulting Pd-nanoparticles constitute stable and reusable catalysts for the synthesis of various N-alkyl amines using borrowing hydrogen technology without the use of any base or additive. By applying this Pd-based catalyst, functionalized and structurally diverse N-alkylated amines as well as some selected drug molecules were synthesized in good to excellent yields. Practical and synthetic utility of this Pd-based amination protocol has been demonstrated by upscaling catalyst preparation and amination reactions to several grams-scales as well as recycling of catalyst. Noteworthy, this Pd-catalyst preparation has been up-scaled to kilogram scale and catalysts prepared in both small (1 g) and large-scale (kg) exhibited similar structural features and activity.
- Alshammari, Ahmad S.,Natte, Kishore,Kalevaru, Narayana V.,Bagabas, Abdulaziz,Jagadeesh, Rajenahally V.
-
p. 141 - 149
(2020/01/06)
-
- Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
-
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
- Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
-
p. 647 - 654
(2018/10/24)
-
- Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution
-
Control of enantioselectivity remains a major challenge in radical chemistry. The emergence of metalloradical catalysis (MRC) offers a conceptually new strategy for addressing this and other outstanding issues. Through the employment of D2-symmetric chiral amidoporphyrins as the supporting ligands, Co(II)-based MRC has enabled the development of new catalytic systems for asymmetric radical transformations with a unique profile of reactivity and selectivity. With the support of new-generation HuPhyrin chiral ligands whose cavity environment can be fine-tuned, the Co-centered d-radicals enable to address challenging issues that require exquisite control of fundamental radical processes. As showcased with asymmetric 1,5-C-H amination of sulfamoyl azides, the enantiocontrol of which has proven difficult, the judicious use of HuPhyrin ligand by tuning the bridge length and other remote nonchiral elements allows for controlling both the degree and sense of asymmetric induction in a systematic manner. This effort leads to successful development of new Co(II)-based catalytic systems that are highly effective for enantiodivergent radical 1,5-C-H amination, producing both enantiomers of the strained five-membered cyclic sulfamides with excellent enantioselectivities. Detailed deuterium-labeling studies, together with DFT computation, have revealed an unprecedented mode of asymmetric induction that consists of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution.
- Lang, Kai,Torker, Sebastian,Wojtas, Lukasz,Zhang, X. Peter
-
supporting information
p. 12388 - 12396
(2019/08/20)
-
- INHIBITORS OF N-ACYLPHOSPHATIDYLETHANOLAMINE PHOSPHOLIPASE D (NAPE-PLD)
-
The invention relates to a compound of the formula (I) as novel inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD), and to use thereof for the prophylaxis or treatment of diseases associated with NAPE-PLD. wherein in a ring A, X1 is N, or CR4; X2 is N or CR5; X3 is N or CH; with the proviso that at least one of X1 and X3 is N.
- -
-
-
- TRNA SYNTHETASE INHIBITORS
-
Disclosed herein are secondary amine compounds that inhibit tRNA synthetase. The compounds of the invention are useful in inhibiting tRNA synthetase in Gram-negative bacteria and are useful in killing Gram-negative bacteria. The secondary amine compounds of the invention are also useful in the treatment of tuberculosis.
- -
-
Paragraph 00165-00167; 00223
(2019/07/30)
-
- Direct Reductive N-Functionalization of Aliphatic Nitro Compounds
-
The first general protocol for the direct reductive N-functionalization of aliphatic nitro compounds is presented. The nitro group is partially reduced to a nitrenoid, with a mild and readily available combination of B2pin2 and zinc organyls. Thereby, the formation of an unstable nitroso intermediate is avoided, which has so far severely limited reductive transformations of aliphatic nitro compounds. The reaction is concluded by an electrophilic amination of zinc organyls.
- Rauser, Marian,Ascheberg, Christoph,Niggemann, Meike
-
p. 3970 - 3974
(2018/02/26)
-
- Lithium-Catalyzed anti-Markovnikov Intermolecular Hydroamination Reactions of Vinylarenes and Simple Secondary Amines
-
Various β-arylethylamine derivatives were straightforwardly obtained by the lithium-catalyzed anti-Markovnikov selective intermolecular hydroamination reaction of secondary aliphatic amines with vinylarenes. The use of only 1.5 mol % LiCH2TMS as a solid base in THF proved to be efficient to deliver the target products at room temperature with up to complete conversions. Both reaction partners were, moreover, used in equivalent amounts; thus, this protocol best respects the concepts of sustainable chemistry for the easy preparation of lead structures for pharmaceutically active compounds.
- Germain, Stéphane,Lecoq, Meije,Schulz, Emmanuelle,Hannedouche, Jér?me
-
p. 1749 - 1753
(2017/05/26)
-
- Acidic solvent-free removal of amine-protecting diphenylmethyl groups in the presence of camphorsulfonic acid
-
We developed novel reaction conditions for the removal of the diphenylmethyl group, which is one of the most important protecting groups for amines. The reaction was promoted by adding one equivalent of camphorsulfonic acid in aqueous media, and no acidic
- Yamagiwa, Noriyuki,Okabe, Takayuki,Suto, Yutaka,Iwasaki, Genji
-
p. 1456 - 1458
(2017/11/04)
-
- Highly Efficient Rh(I) Homo- and Heterogeneous Catalysts for C-N Couplings via Hydrogen Borrowing
-
Rhodium(I) complexes were explored as catalysts for the hydrogen borrowing reactions of amines and alcohols. Bidentate carbene-triazole ligands were readily synthesized via "click" reactions which allowed a diversity of ligand backbones to be accessed. The catalytic transformations are highly efficient, able to reach completion in under 6 h, and promote C-N bond formation across a range of primary alcohol and amine substrates. Moreover, site-selective catalysis can be achieved using substrates with more than one reactive site. A rhodium(I) complex covalently attached to a carbon black surface was also deployed in the hydrogen borrowing coupling reaction of aniline with benzyl alcohol. This represents the first report of a heterogeneous rhodium catalyst used for hydrogen borrowing.
- Wong, Chin M.,Peterson, Matthew B.,Pernik, Indrek,McBurney, Roy T.,Messerle, Barbara A.
-
supporting information
p. 14682 - 14687
(2017/12/15)
-
- Iridium(I) Complexes Bearing a Noninnocent PNP-Pincer-Type Phosphaalkene Ligand: Catalytic Application in the Base-Free N-Alkylation of Amines with Alcohols
-
A series of IrI complexes [Ir(L)(PPEP?)] [L = Cl- (3), CO (4), tBuNC (5), PMe3 (6), PPh3 (7)], coordinated with a PNP-pincer-type phosphaalkene ligand bearing a dearomatized pyridine ring (PPEP?), have been prepared and their catalytic properties for the dehydration/condensation of amines with alcohols has been examined. The catalytic reactions successfully proceed under base-free conditions to give N-alkylated amines and their dehydrogenation derivatives (imines). The product selectivity is dependent on L coordinated with Ir(PPEP?). Complexes 4 and 5 that contain π-accepting ligands (CO, tBuNC) form N-alkylated amines as the major products in a closed system using a nitrogen-gas-filled Schlenk tube. In contrast, complex 7 that contain PPh3 as L produces imines as the major products under a nitrogen-gas flow. The reason for the selectivity change depending on L is discussed based on stoichiometric reactions using model compounds of presumed catalytic intermediates. PNP-pincer-type phosphaalkene complexes of IrI bearing a dearomatized pyridine ring have been found to catalyze the dehydration/condensation of amines with alcohols under base-free conditions to afford N-alkylated amines and imines in high yields. The product selectivity can be controlled by the choice of auxiliary ligands (L) as well as the reaction conditions.
- Chang, Yung-Hung,Tanigawa, Ippei,Taguchi, Hiro-Omi,Takeuchi, Katsuhiko,Ozawa, Fumiyuki
-
p. 754 - 760
(2016/03/01)
-
- Cobalt-Catalyzed N-Alkylation of Amines with Alcohols
-
A well-defined nonprecious metal cobalt(II) catalyst based on a pincer PNP ligand has been employed for the efficient N-alkylation of both aromatic and aliphatic amines with alcohols. A subtle change of reaction conditions (simply adding 4 ? molecular sieves) was observed to readily switch the resulting products (amines vs imines) with high chemoselectivity. A range of alcohols and amines including both aromatic and aliphatic substrates were efficiently converted to secondary amines in good-to-excellent yields when 2 mol % cobalt catalyst was used. Additional experiments indicate that a hydrogen-borrowing mechanism is responsible for the tandem acceptorless dehydrogenation/condensation/hydrogenation process.
- Zhang, Guoqi,Yin, Zhiwei,Zheng, Shengping
-
supporting information
p. 300 - 303
(2016/02/03)
-
- Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions
-
NHC-rhodium complexes (NHC=N-heterocyclic carbenes) have been widely used as efficient catalysts for hydrosilylation reactions. However, the substrates were mostly limited to reactive carbonyl compounds (aldehydes and ketones) or carbon-carbon multiple bonds. Here, we describe the application of newly-developed chelating bis(tzNHC)-rhodium complexes (tz=1,2,3-triazol-5-ylidene) for several reductive transformations. With these catalysts, the formal reductive methylation of amines using carbon dioxide, the hydrosilylation of amides and carboxylic acids, and the reductive alkylation of amines using carboxylic acids have been achieved under mild reaction conditions.
- Nguyen, Thanh V. Q.,Yoo, Woo-Jin,Kobayashi, Shu
-
supporting information
p. 452 - 458
(2016/02/12)
-
- Benzylamines via Iron-Catalyzed Direct Amination of Benzyl Alcohols
-
Benzylamines play a prominent role in numerous pharmaceutically active compounds. Thus, the development of novel, sustainable catalytic methodologies to provide access to these privileged structural motifs is of central importance. Herein we describe a systematic study for the construction of a large variety of benzylamines using a well-defined homogeneous iron complex. The methodology consists of the direct coupling of readily available benzyl alcohols with simpler amines through the borrowing hydrogen methodology, producing a variety of substituted secondary and tertiary benzylamines in moderate to excellent yields for the first time with an iron catalyst. Notably, we explore the versatility of this methodology in the one-pot synthesis of nonsymmetric tertiary amines, sequential functionalization of diols with distinctly different amines, and the synthesis of N-benzyl piperidines via various synthetic pathways. In addition, direct conversion of the renewable building block 2,5-furan-dimethanol to pharmaceutically relevant compounds is achieved.
- Yan, Tao,Feringa, Ben L.,Barta, Katalin
-
p. 381 - 388
(2016/01/12)
-
- Novel bis-arylalkylamines as myeloperoxidase inhibitors: Design, synthesis, and structure-activity relationship study
-
Human myeloperoxidase (MPO) plays an important role in innate immunity but also aggravates tissue damage by oxidation of biomolecules at sites of inflammation. As a result from a recent high-throughput virtual screening approach for MPO inhibitors, bis-2,2′-[(dihydro-1,3(2H,4H) pyrimidinediyl)bis(methylene)]phenol was detected as a promising lead compound for inhibition of the MPO-typical two-electron oxidation of chloride to hypochlorous acid (IC50= 0.5 μM). In the present pharmacomodulation study, 37 derivatives of this lead compound were designed and synthesized driven by comprehensive docking studies and the impact on the chlorination activity of MPO. We describe the structural requirements for optimum (i) binding to the heme periphery and (ii) inhibition capacity. Finally, the best three inhibitors (bis-arylalkylamine derivatives) were probed for interaction with the MPO redox intermediates Compound I and Compound II. Determined apparent bimolecular rate constants together with determination of reduction potential and nucleophilicity of the selected compounds allowed us to propose a mechanism of inhibition. The best inhibitor was found to promote the accumulation of inactive form of MPO-Compound II and has IC50= 54 nM, demonstrating the successful approach of the drug design. Due to the similarity of ligand interactions between MPO and serotonine transporter, the selectivity of this inhibitor was also tested on the serotonin transporter providing a selectivity index of 14 (KiSERT/IC50MPO).
- Aldib, Iyas,Gelbcke, Michel,Soubhye, Jalal,Prévost, Martine,Furtmüller, Paul G.,Obinger, Christian,Elfving, Betina,Alard, Ibaa Chikh,Roos, Goedele,Delporte, Cédric,Berger, Gilles,Dufour, Damien,Zouaoui Boudjeltia, Karim,Nève, Jean,Dufrasne, Francois,Van Antwerpen, Pierre
-
supporting information
p. 746 - 762
(2016/08/18)
-
- Tunable dehydrogenative amidation versus amination using a single ruthenium-NHC catalyst
-
Mixed N-heterocyclic carbene (NHC)/phosphine complexes of the type [RuCl(p-cymene)(bimy)(PPh3)]- PF6 (bimy = benzimidazolin-2-ylidene) have been synthesized and fully characterized. Complex 1 bearing the 1,3-dibenzylbenzimidazolin-2-ylidene ligand is able to selectively catalyze both dehydrogenative amidation, mono-, and diamination (N-alkylation) through coupling of simple alcohols with amines effectively yielding a range of amides and secondary and tertiary amines. Selectivity is achieved by controlling the fate of the common hemiaminal intermediate, which in turn can be simply influenced by the choice of base and solvent.
- Xie, Xiaoke,Huynh, Han Vinh
-
p. 4143 - 4151
(2015/11/11)
-
- Method of producing higher amine (by machine translation)
-
PROBLEM TO BE SOLVED: To provide a method of producing a secondary or tertiary higher amine. SOLUTION: The method of producing a higher amine comprises allowing a primary or secondary amine to react with an alcohol in the presence of at least one species of hydrogen halide selected from hydrogen chloride, hydrogen bromide and hydrogen iodide, or in the presence of a compound capable of producing a hydrogen halide (such as 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride). If the raw material amine is a primary amine, a secondary higher amine and a tertiary higher amine can be produced. If the raw material amine is a secondary amine, a tertiary higher amine can be produced. COPYRIGHT: (C)2012,JPO&INPIT
- -
-
Paragraph 0048; 0073; 0074
(2016/10/08)
-
- Selective and recyclable rhodium nanocatalysts for the reductive N-alkylation of nitrobenzenes and amines with aldehydes
-
Rhodium nanocatalysts were prepared and applied for the reductive N-alkylation of nitrobenzenes and amines to the corresponding secondary amines with aldehydes and ketones. Functional nitrobenzenes, such as nitrobenzenes with F, Cl, Br, CH3O and CH3 were transformed to the corresponding secondary amines in good to excellent yields. Moreover, the Rh@CN catalyzed N-alkylation of a series of primary amines with aldehydes and ketones also gave the corresponding secondary amines in high yields. The Rh@CN is heterogeneous, and can be reusable several times (at least 4 times) for the reductive N-alkylation of nitroarenes.
- Huang, Lei,Wang, Zhi,Geng, Longfei,Chen, Rizhi,Xing, Weihong,Wang, Yong,Huang, Jun
-
p. 56936 - 56941
(2015/07/15)
-
- Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions
-
An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2]2, with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.
- Lee, Jeongbin,Muthaiah, Senthilkumar,Hong, Soon Hyeok
-
p. 2653 - 2660
(2014/09/17)
-
- Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology
-
Using a simple amino amide ligand, ruthenium-catalyzed one-pot alkylation of primary and secondary amines with simple alcohols was carried out under a wide range of conditions. Using the alcohol as solvent, alkylation was achieved under mild conditions, even as low as room temperature. Reactions occurred with high conversion and selectivity in many cases. Reactions can also be carried out at high temperatures in organic solvent with high selectivity using stoichiometric amounts of the alcohol.
- Enyong, Arrey B.,Moasser, Bahram
-
p. 7553 - 7563
(2014/09/17)
-
- Solid base catalyzed highly efficient N-alkylation of amines with alcohols in a solvent-free system
-
Different from any other catalytic systems containing transition metals and additives, sodium hydroxide itself was found to be a unique and effective catalyst for the solvent-free synthesis of the secondary amines via the N-alkylation of amines with alcohols. For the reaction of aniline with benzyl alcohol, 99.6 mol% conversion of aniline and 99.5% selectivity of the product were achieved under optimal conditions. Also, high conversion and selectivity could be acquired for the N-alkylations of various amines with alcohols, implying the universality of this methodology. Mechanistic studies revealed that this novel reaction most possibly proceeds with a base-catalyzed mechanism.
- Lu,Sun,Wei,Peng,Zhou,Xia
-
-
- Selective N-alkylation of primary amines with R-NH2·HBr and alkyl bromides using a competitive deprotonation/protonation strategy
-
Monoalkylation of primary amines using amine hydrobromides and alkyl bromides has been carried out. Under controlled reaction conditions the reactant primary amine was selectively deprotonated and made available for reaction, while the newly generated secondary amine remained protonated, and did not participate in alkylation further. Reaction was carried out under mild reaction conditions and was applicable to a wide range of primary amines and alkyl bromides.
- Bhattacharyya, Shubhankar,Pathak, Uma,Mathur, Sweta,Vishnoi, Subodh,Jain, Rajeev
-
p. 18229 - 18233
(2014/05/20)
-
- Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst
-
An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.
- Yim, Jacky C.-H.,Bexrud, Jason A.,Ayinla, Rashidat O.,Leitch, David C.,Schafer, Laurel L.
-
p. 2015 - 2028
(2014/04/03)
-
- Ruthenium-catalyzed direct reductive amination in HCOOH/NEt3 mixture
-
A one-pot direct reductive amination of aldehydes with primary and secondary amines using Noyori's catalyst (η 6-arene)Ru(H)TsDPEN in neat HCOOH/NEt3 mixture has been developed. The catalyst formed in situ allows full conversion of aldehydes with high selectivities towards the desired amine products within hours or even minutes at room temperature. For aromatic aldehydes, both 5:2 and 5:3 HCOOH/NEt3 mixtures prove to be suitable reaction media, with the former affording higher selectivities while the latter leading to much faster reaction rates. For aliphatic aldehydes, the 5:3 HCOOH/NEt3 mixture gives much higher selectivities due to the minimal loss from aldol condensation. This method has great application potential for the synthesis of amine products given the mild conditions. Graphical Abstract: [Figure not available: see fulltext.]
- Zhu, Mengping
-
p. 1568 - 1572,5
(2014/10/15)
-
- Heteroleptic alkyl and amide iminoanilide alkaline earth and divalent rare earth complexes for the catalysis of hydrophosphination and (Cyclo) hydroamination reactions
-
[{N^N}M(X)(thf)n] alkyl (X=CH(SiMe3)2) and amide (X=N(SiMe3)2) complexes of alkaline earths (M=Ca, Sr, Ba) and divalent rare earths (YbII and EuII) bearing an iminoanilide ligand ({N^N}-) are presented. Remarkably, these complexes proved to be kinetically stable in solution. X-ray diffraction studies allowed us to establish size-structure trends. Except for one case of oxidation with [{N^N}YbII{N(SiMe3)2}(thf)], all these complexes are stable under the catalytic conditions and constitute effective precatalysts for the cyclohydroamination of terminal aminoalkenes and the intermolecular hydroamination and intermolecular hydrophosphination of activated alkenes. Metals with equal sizes across alkaline earth and rare earth families display almost identical apparent catalytic activity and selectivity. Hydrocarbyl complexes are much better catalyst precursors than their amido analogues. In the case of cyclohydroamination, the apparent activity decreases with metal size: Ca>Sr>Ba, and the kinetic rate law agrees with R CHA=k[precatalyst]1[aminoalkene]1. The intermolecular hydroamination and hydrophosphination of styrene are anti-Markovnikov regiospecific. In both cases, the apparent activity increases with the ionic radius (CaHA=k[styrene]1[amine]1[precatalyst] 1 and RHP=k[styrene]1[HPPh2] 0[precatalyst]1, respectively. Mechanisms compatible with the rate laws and kinetic isotopic effects are proposed. [{N^N}Ba{N(SiMe 3)2}(thf)2] (3) and [{N^N}Ba{CH(SiMe 3)2}(thf)2] (10) are the first efficient Ba-based precatalysts for intermolecular hydroamination and hydrophosphination, and display activity values that are above those reported so far. The potential of the precatalysts for C-N and C-P bond formation is detailed and a rare cyclohydroamination-intermolecular hydroamination "domino" sequence is presented. Activated alkenes: Long sought heteroleptic alkyl and amide complexes of large alkaline earths (Ca, Sr, Ba) and divalent rare earths (Yb, Eu) supported by a bulky iminoanilide ancillary ligand have been prepared (see figure). These complexes are very versatile, active, and selective in the catalysis of the cyclohydroamination of aminoalkenes, and the intermolecular hydroamination and hydrophosphination of activated alkenes. Copyright
- Liu, Bo,Roisnel, Thierry,Carpentier, Jean-Francois,Sarazin, Yann
-
p. 13445 - 13462
(2013/10/08)
-
- Pt/C catalysed direct reductive amination of nitriles with primary amines in a continuous flow multichannel microreactor
-
Aliphatic and aromatic secondary amines were synthesised selectively by one pot reductive amination of nitriles with primary amines using Pt/C (3% by weight) catalyst in a continuous flow multichannel microreactor. Molecular hydrogen was used as a clean reducing agent at moderate reaction conditions. The Royal Society of Chemistry 2013.
- Sharma, Sumeet K.,Lynch, James,Sobolewska, Anna M.,Plucinski, Pawel,Watson, Robert J.,Williams, Jonathan M. J.
-
-
- A bis(phosphaethenyl)pyridine complex of iridium(I): Synthesis and catalytic application to N-alkylation of amines with alcohols
-
The iridium(I) complex [IrCl(BPEP-H)] (1), coordinated with 2,6-bis[2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyl]pyridine (BPEP-H) as a PNP-pincer-type phosphaalkene ligand, has been synthesized and fully characterized by elemental analysis, NMR spectroscopy, and X-ray diffraction analysis. Complex 1 (1 mol %) catalyzes N-alkylation of primary and secondary amines with alcohols, leading to the selective formation of secondary and tertiary amines, respectively. Primary amines are smoothly alkylated with a variety of benzylic and aliphatic alcohols (1 or 3 equiv) at 100 C under basic conditions (CsOH, 10 mol %) to give the corresponding secondary amines in good to high yields. On the other hand, N-alkylation of secondary amines with benzyl alcohol (3 equiv) proceeds in the presence of KH2PO4 (5 mol %) at 140 C to afford tertiary amines in high yields.
- Chang, Yung-Hung,Nakajima, Yumiko,Ozawa, Fumiyuki
-
p. 2210 - 2215
(2013/05/21)
-
- Nickel-catalysed reductive amination with hydrosilanes
-
That's just silyl! Selective nickel-catalyzed reductive amination of aldehydes under hydrosilylation conditions is achieved by using a one pot, two step procedure. By using an insitu-generated catalyst (5mol%) from Ni(OAc)2 and tricyclohexylphosphine with tetramethyldisiloxane (TMDS) as the hydrosilane at 70°C, the corresponding secondary amines were obtained in moderate to good isolated yields.
- Zheng, Jianxia,Roisnel, Thierry,Darcel, Christophe,Sortais, Jean-Baptiste
-
p. 2861 - 2864
(2013/10/21)
-
- Heavier alkaline earth catalysts for the intermolecular hydroamination of vinylarenes, dienes, and alkynes
-
The heavier group 2 complexes [M{N(SiMe3)2} 2]2(1, M = Ca; 2, M = Sr) and [M{CH(SiMe3) 2}2(THF)2] (3, M = Ca; 4, M = Sr) are shown to be effective precatalysts for the intermolecular hydroamination of vinyl arenes and dienes under mild conditions. Initial studies revealed that the amide precatalysts, 1 and 2, while compromised in terms of absolute activity by a tendency toward transaminative behavior, offer greater stability toward polymerization/oligomerization side reactions. In every case the strontium species, 2 and 4, were found to outperform their calcium congeners. Reactions of piperidine with para-substituted styrenes are indicative of rate-determining alkene insertion in the catalytic cycle while the ease of addition of secondary cyclic amines was found to be dependent on ring size and reasoned to be a consequence of varying amine nucleophilicity. Hydroamination of conjugated dienes yielded isomeric products via η3-allyl intermediates and their relative distributions were explained through stereoelectronic considerations. The ability to carry out the hydroamination of internal alkynes was found to be dramatically dependent upon the identity of the alkyne substituents while reactions employing terminal alkynes resulted in the precipitation of insoluble and unreactive group 2 acetylides. The rate law for styrene hydroamination with piperidine catalyzed by [Sr{N(SiMe3) 2}2]2 was deduced to be first order in [amine] and [alkene] and second order in [catalyst], while large kinetic isotope effects and group 2 element-dependent ΔS? values implicated the formation of an amine-assisted rate-determining alkene insertion transition state in which there is a considerable entropic advantage associated with use of the larger strontium center.
- Brinkmann, Christine,Barrett, Anthony G. M.,Hill, Michael S.,Procopiou, Panayiotis A.
-
supporting information; experimental part
p. 2193 - 2207
(2012/03/10)
-
- When bigger is better: Intermolecular hydrofunctionalizations of activated alkenes catalyzed by heteroleptic alkaline earth complexes
-
New alkaline-earth amido complexes catalyze the regioselective intermolecular hydroamination (see scheme; Ae=alkaline earth) and hydrophosphination of styrene and isoprene with unprecedented activities. The catalytic performances increased linearly with the size of the metal. Copyright
- Liu, Bo,Roisnel, Thierry,Carpentier, Jean-Francois,Sarazin, Yann
-
supporting information; experimental part
p. 4943 - 4946
(2012/07/13)
-
- Synthesis and spectral studies on Pb(II) dithiocarbamate complexes containing benzyl and furfuryl groups and their use as precursors for PbS nanoparticles
-
Nine lead bis(dithiocarbamate) complexes based on benzyl and furfuryl groups have been prepared. The complexes were characterized using IR and NMR spectroscopy. All the complexes showed the expected signals in 1H and 13C NMR spectra associated with the dithiocarbamate ligands. IR and 13C NMR spectral studies indicate that the S2CN double bond character increases with increase in length of alkyl chain bonded to nitrogen atom. Bis(N-benzyl-N-(2-phenylethyl)dithiocarbamato-S,S′)lead(II) (3) and bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S′)lead(II) (4) have been used as single source precursors for the synthesis of ethylenediamine capped PbS nanoparticles. Powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), FTIR, UV-vis and fluorescence spectroscopy have been used to characterize the as-prepared lead sulfide nanoparticles. The PXRD measurements suggest that PbS nanoparticles are single phase with face-centered-cubic structure.
- Sathiyaraj, Ethiraj,Thirumaran, Subbiah
-
p. 575 - 581,7
(2012/12/11)
-
- Coupling of two multistep catalytic cycles for the one-pot synthesis of propargylamines from alcohols and primary amines on a nanoparticulated gold catalyst
-
A one-pot reaction was performed with a nanoparticulated gold catalyst. A secondary amine is formed through N-monoalkylation of a primary amine with an alcohol by a borrowing hydrogen methodology in a three-step reaction. The secondary amine formed enters into a second A3-coupling cycle to give propargylamines. The multistep reaction requires a gold species formed and stabilized on a ceria surface. Copyright
- Corma, Avelino,Navas, Javier,Sabater, Maria J.
-
p. 14150 - 14156
(2013/01/15)
-
- Ruthenium(II) picolyl-NHC complexes: Synthesis, characterization, and catalytic activity in amine N-alkylation and transfer hydrogenation reactions
-
Ruthenium(II) p-cymene complexes with picolyl-functionalized N-heterocyclic carbenes [(η6-p-cymene)Ru(L)(Cl)][PF6] (L = 3-methyl-1-(2-picolyl)imidazol-2-ylidene (1a), 3-isopropyl-1-(2-picolyl) imidazol-2-ylidene (1b), 3,4,5-trimethyl-1-(2-picolyl)imidazol-2-ylidene (1c), 3-mesityl-1-(2-picolyl)imidazol-2-ylidene (1d), 3-methyl-1-(2-picolyl) benzoimidazol-2-ylidene (1e), 3-methyl-1-(2-picolyl)-4,5-dichloroimidazol-2- ylidene (1f), 3-phenyl-1-(2-picolyl)imidazol-2-ylidene (1g)) have been synthesized and characterized. Compounds 1a-g were recrystallized, and X-ray crystal structures are reported for 1a,f. Furthermore, compounds 1a-f show catalytic activity in transfer hydrogenation of ketones and N-alkylation of amines. Notably, complexes 1a,c,f were found to be very efficient and versatile catalysts toward transfer hydrogenation of a wide range of ketones and imines in addition to N-alkylation of several amines.
- Fernandez, Francys E.,Puerta, M. Carmen,Valerga, Pedro
-
p. 6868 - 6879
(2012/11/13)
-
- Palladium-catalyzed double carbonylation using near stoichiometric carbon monoxide: Expedient access to substituted 13C2-labeled phenethylamines
-
A novel and general approach for 13C2- and 2H-labeled phenethylamine derivatives has been developed, based on a highly convergent single-step assembly of the carbon skeleton. The efficient incorporation of two carbon-13 isotopes into phenethylamines was accomplished using a palladium-catalyzed double carbonylation of aryl iodides with near stoichiometric carbon monoxide.
- Nielsen, Dennis U.,Neumann, Karoline,Taaning, Rolf H.,Lindhardt, Anders T.,Modvig, Amalie,Skrydstrup, Troels
-
p. 6155 - 6165
(2012/09/21)
-
- Reductive hydroxyalkylation/alkylation of amines with lactones/esters
-
We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.
- Wang, Yu-Huang,Ye, Jian-Liang,Wang, Ai-E,Huang, Pei-Qiang
-
p. 6504 - 6511
(2012/09/08)
-
- A general and selective copper-catalyzed reduction of secondary amides
-
In situ-generated cationic copper/pybox catalyst systems allow for the selective reduction of secondary amides into the corresponding amines under mild conditions. This novel protocol has a wide substrate scope and shows good functional group tolerance. The Royal Society of Chemistry 2012.
- Das, Shoubhik,Join, Benoit,Junge, Kathrin,Beller, Matthias
-
p. 2683 - 2685
(2012/04/04)
-
- Selective N-alkylation of amines with alcohols by using non-metal-based acid-base cooperative catalysis
-
Learning to cooperate: A straightforward method for the selective N-mono- and dialkylation of amines with alcohols by means of non-metal-based catalysis promoted by TAPC is reported (see scheme). Selectivity of the N-mono- and dialkylation, substrate scope and functional-group tolerance are highlighted with respect to each amine (1° and 2°; aromatic and aliphatic) and alcohol (1°, 2° and 3°; benzylic and aliphatic) component. Copyright
- Du, Ya,Oishi, Shunsuke,Saito, Susumu
-
supporting information; experimental part
p. 12262 - 12267
(2011/11/29)
-
- Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides: mild, efficient, and selective removal of N-tosyl group
-
Hg cathode-free electrochemical detosylation of N,N-disubstituted p-toluenesulfonamides was successfully carried out by a constant current electrolysis using an undivided cell equipped with a platinum cathode and a magnesium anode in the presence of an arene mediator. The deprotection proceeded efficiently and selectively under neutral and mild conditions with a stoichiometric amount of electricity without the use of an Hg cathode to obtain the corresponding secondary amines in good to excellent yields.
- Senboku, Hisanori,Nakahara, Kazuo,Fukuhara, Tsuyoshi,Hara, Shoji
-
supporting information; experimental part
p. 435 - 438
(2010/03/04)
-
- Heavier group 2 metals and intermolecular hydroamination: A computational and synthetic assessment
-
(Chemical Equation Presented) A density functional theory assessment of the use of the group 2 elements Mg, Ca, Sr, and Ba for the intermolecular hydroamination of ethene indicated that the efficiency of the catalysis is dependent upon both the polarity and the deformability of the electron density within the metal-substituent bonds of key intermediates and transition states. The validity of this analysis was supplemented by a preliminary study of the use of group 2 amides for the intermolecular hydroamination of vinyl arenes. Although strontium was found to provide the highest catalytic activity, in line with the expectation provided by the theoretical study, a preliminary kinetic analysis demonstrated that this is possibly a consequence of the increased radius and accessibility of this cation rather than a reflection of a reduced barrier for rate-determining alkene insertion.
- Barrett, Anthony G. M.,Brinkmann, Christine,Crimmin, Mark R.,Hill, Michael S.,Hunt, Patricia,Procopiou, Panayiotis A.
-
scheme or table
p. 12906 - 12907
(2009/12/05)
-