- BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
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A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.
- Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin
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supporting information
p. 5205 - 5211
(2021/07/29)
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- Integrated Electro-Biocatalysis for Amine Alkylation with Alcohols
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The integration of electro and bio-catalysis offers new ways of making molecules under very mild, environmentally benign conditions. We show that TEMPO mediated electro-catalytic oxidation of alcohols can be adapted to work in aqueous buffers, with minimal organic co-solvent, enabling integration with biocatalytic reductive amination using the AdRedAm enzyme. The combined process offers a new approach to amine alkylation with native alcohols, a key bond formation in the chemical economy that is currently achieved via precious metal-catalyzed hydrogen-borrowing technologies. The electrobio transformation is effective for primary and secondary alcohols undergoing coupling with allyl, propargyl, benzyl, and cyclopropyl amines, and has been adapted for use with solid-supported AdRedAm for ease of operation.
- Pe?afiel, Itziar,Dryfe, Robert A. W.,Turner, Nicholas J.,Greaney, Michael F.
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p. 864 - 867
(2021/01/21)
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- Sequential hydroaminomethylation/Pd-catalyzed hydrogenolysis as an atom efficient route to valuable primary and secondary amines
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The facile synthesis of valuable primary and secondary amines is reported using a sequential procedure of hydroaminomethylation and Pd-catalyzed hydrogenolysis. The hydroaminomethylation reaction was catalyzed by a cationic Rh(I) iminopyridyl complex and the N-alkylated benzylamines were produced with high chemoselectivity, albeit as mixtures of linear and branched products. Performing the hydrogenolysis reaction using 10% Pd/C, provided access to valuable primary and secondary amines which have applications in the surfactant, pharmaceutical and polymer industries.
- October, Jacquin,Mapolie, Selwyn F.
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supporting information
(2021/04/12)
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- Intramolecular C?H Amination of N-Alkylsulfamides by tert-Butyl Hypoiodite or N-Iodosuccinimide
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1,3-Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C?H amination of N-alkylsulfamide derivatives is a reliable method for the construction of 1,3-diamine structures, the majority of these methods involve the use of a transition-metal catalyst. We herein report on a new transition-metal-free method using tert-butyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS), enabling secondary non-benzylic and tertiary C?H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3-diamines. Mechanistic investigations revealed that amination reactions using t-BuOI or NIS each proceed via different pathways.
- Kiyokawa, Kensuke,Jou, Keisuke,Minakata, Satoshi
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supporting information
p. 13971 - 13976
(2021/08/30)
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- One-Pot Controlled Reduction of Conjugated Amides by Sequential Double Hydrosilylation Catalyzed by an Iridium(III) Metallacycle
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A single and accessible cationic iridiumIII metallacycle effectively catalyzes the one-pot sequential double hydrosilylation of challenging α,β-unsaturated secondary and tertiary amides to afford, in a controlled and straightforward way, the co
- Agbossou-Niedercorn, Francine,Corre, Yann,Djukic, Jean-Pierre,Kalocsai, Dorottya,Michon, Christophe,Nagyházi, Márton,Rysak, Vincent,Trivelli, Xavier
-
supporting information
p. 6212 - 6220
(2020/10/02)
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- Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations
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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
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p. 3508 - 3514
(2020/06/02)
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- Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate
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Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- A nd nine-membered benzolactams.
- Kurouchi, Hiroaki,Ohwada, Tomohiko
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p. 876 - 901
(2019/12/30)
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- Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines
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We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.
- Beller, Matthias,Chandrashekhar, Vishwas G.,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kalevaru, Narayana V.,Kamer, Paul C. J.,Senthamarai, Thirusangumurugan,Zbo?il, Radek
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p. 2973 - 2981
(2020/03/27)
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- PRODUCTION OF AMINES VIA A HYDROAMINOALKYLATION REACTION
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Provided is a process for producing an amine via a hydroaminoalkylation reaction of a non-aromatic C-C double bond or C-C triple bond, said process comprising a step of reacting a compound comprising a non-aromatic C-C double bond or C-C triple bond with a reactive component which is obtainable by combining an aminal or a hemiaminal ether with an acidic medium comprising trifluoroacetic acid, wherein the aminal contains two amino groups independently selected from a secondary and a tertiary amino group that are linked by a methylene group wherein one hydrogen atom may be replaced by a further substituent, and at least one of the amino groups carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the hemiaminal ether contains a secondary or a tertiary amino group which carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the secondary or tertiary amino group is linked to an alkoxy group by a methylene group wherein one hydrogen atom may be replaced by a further substituent.
- -
-
Page/Page column 64-65; 72-73
(2019/12/04)
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- A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes
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In comparison to the extensively studied metal-catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench-stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.
- Kaiser, Daniel,Tona, Veronica,Gon?alves, Carlos R.,Shaaban, Saad,Oppedisano, Alberto,Maulide, Nuno
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p. 14639 - 14643
(2019/09/17)
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- Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
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The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.
- Ramsden, Jeremy I.,Heath, Rachel S.,Derrington, Sasha R.,Montgomery, Sarah L.,Mangas-Sanchez, Juan,Mulholland, Keith R.,Turner, Nicholas J.
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p. 1201 - 1206
(2019/01/21)
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- Iron-Catalyzed Reductive Amination of Aldehydes in Isopropyl Alcohol/Water Media as Hydrogen Sources
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Reductive amination can be carried in i-PrOH/H2O as hydrogen sources using commercially available iron carbonyl complexes. Within an aqueous alkaline environment, a hydridocarboferrate is formed and its reducing potential is exploited for hydrogenation of the imine (or iminium ion) obtained in situ from aldehydes or ketones, and primary or secondary amines in almost equimolar ratio. This completely sustainable and hydrogen-free process proceeds at 100 °C using Fe3(CO)12 as catalyst precursor under convectional heating while Fe2(CO)9 gave better results when the reaction was carried out under MW dielectric heating. Both enolizable and non-enolizable aldehydes may be successfully employed in reactions with aliphatic and aromatic amines. (Figure presented.).
- Petricci, Elena,Santillo, Niccolò,Castagnolo, Daniele,Cini, Elena,Taddei, Maurizio
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supporting information
p. 2560 - 2565
(2018/07/29)
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- Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing
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The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.
- Montgomery, Sarah L.,Mangas-Sanchez, Juan,Thompson, Matthew P.,Aleku, Godwin A.,Dominguez, Beatriz,Turner, Nicholas J.
-
supporting information
p. 10491 - 10494
(2017/08/22)
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- Novel bis-arylalkylamines as myeloperoxidase inhibitors: Design, synthesis, and structure-activity relationship study
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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)
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- Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions
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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
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p. 2653 - 2660
(2014/09/17)
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- Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
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A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
- Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
-
supporting information
p. 3683 - 3690
(2014/05/20)
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- Rhodium-catalyzed highly regioselective hydroaminomethylation of styrenes with tetraphosphorus ligands
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The highly linear-selective hydroaminomethylation of styrenes is very challenging. Herein, an efficient, highly chemoselective, and linear-selective hydroaminomethylation (l/b up to >99:1) of styrenes using Rh(nbd) 2SbF6 with a pyrrole-based 3,3′,5,5′- substituted tetraphosphorus ligand is documented. This is in sharp contrast to other available processes leading to branched amines and provides a novel atom economic approach to 3-arylpropylamines.
- Li, Shengkun,Huang, Kexuan,Zhang, Jiwen,Wu, Wenjun,Zhang, Xumu
-
supporting information
p. 3078 - 3081
(2013/07/26)
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- Development of a solvent selection guide for aldehyde-based direct reductive amination processes
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A range of alternative, more environmentally conservative solvents have been evaluated for use within the direct reductive amination reactions of aldehydes using borane-based reductants. The data generated has been used to develop a guide to facilitate replacement of less desirable chlorinated solvents, such as DCE, from these widely used synthetic processes.
- McGonagle, Fiona I.,MacMillan, Donna S.,Murray, Jane,Sneddon, Helen F.,Jamieson, Craig,Watson, Allan J. B.
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supporting information
p. 1159 - 1165
(2013/06/05)
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- Structure-activity relationships of small molecule inhibitors of RAGE-Aβ binding
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The Receptor for Advanced Glycation Endproducts ('RAGE') mediates transport of amyloid-β peptide (Aβ) into the brain, and is therefore an important target for the development of therapeutic agents for Alzheimer's disease. We describe structure-activity relationships for inhibition of RAGE-Aβ binding, derived from the analysis of a library of tertiary amides.
- Ross, Nathan T.,Deane, Rashid,Perry, Sheldon,Miller, Benjamin L.
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p. 7653 - 7658
(2013/08/23)
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- Pt/C catalysed direct reductive amination of nitriles with primary amines in a continuous flow multichannel microreactor
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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.
-
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- Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane
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Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE) 2Cl]2 with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.
- Cheng, Chen,Brookhart, Maurice
-
supporting information; experimental part
p. 11304 - 11307
(2012/09/05)
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- Conventional and tandem hydroformylation
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Transition-metal-catalyzed hydroformylation has become an essential tool for the synthesis of aldehydes. In this paper, we highlight several examples of synthetically useful applications of homogeneous and heterogeneous rhodium-catalyzed hydroformylation, as well as several examples of tandem processes involving hydroformylation as a reaction step developed in our laboratory.
- Vasylyev, Maksym,Alper, Howard
-
scheme or table
p. 2893 - 2900
(2010/10/21)
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- Borrowing hydrogen methodology for the conversion of alcohols into N-protected primary amines and in situ deprotection
-
Alcohols have been converted into a range of protected amines including sulfonamides and N-alkylbenzylamine derivatives. Representative examples of deprotection to afford primary amines are also provided.
- Lamb, Gareth W.,Watson, Andrew J.A.,Jolley, Katherine E.,Maxwell, Aoife C.,Williams, Jonathan M.J.
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scheme or table
p. 3374 - 3377
(2009/09/05)
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- A biomimetic electrocatalytic system for the atom-economical chemoselective synthesis of secondary amines
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A facile one-pot oxidation-imine formation-reduction route to secondary amines can be achieved electrolytically from primary amines. This atom-economical 1ox-mediated sequence, leaving ammonia as the sole byproduct, allows the rapid chemoselect
- Largeron, Martine,Fleury
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supporting information; experimental part
p. 883 - 886
(2009/07/25)
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- The ruthenium-catalyzed reduction and reductive N-alkylation of secondary amides with hydrosilanes: Practical synthesis of secondary and tertiary amines by judicious choice of hydrosilanes
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(Chemical Equation Presented) A triruthenium cluster, (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7 (1) catalyzes the reaction of secondary amides with hydrosilanes, yielding a mixture of secondary amines, tertiary amines, and silyl enamines. Production of secondary amines with complete selectivity is achieved by the use of higher concentration of the catalyst (3 mol %) and the use of bifunctional hydrosilanes such as 1,1,3,3-tetramethyldisiloxane. Acidic workup of the reaction mixture affords the corresponding ammonium salts, which can be treated with a base, providing a facile method for isolation of secondary amines with high purity. In contrast, tertiary amines are formed with high selectivity by using lower concentration of the catalyst (1 mol %) and polymeric hydrosiloxanes (PMHS) as reducing agent. Reduction with PMHS encapsulates the ruthenium catalyst and organic byproducts to the insoluble silicone resin. The two reaction manifolds are applicable to various secondary amides and are practical in that the procedures provide the desired secondary or tertiary amine as a single product. The product contaminated with only minimal amounts of ruthenium and silicon residues. On the basis of the products and observed side products as well as NMR studies a mechanistic scenario for the reaction is also described.
- Hanada, Shiori,Ishida, Toshiki,Motoyama, Yukihiro,Nagashima, Hideo
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p. 7551 - 7559
(2008/02/12)
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- Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines
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Cerium ammonium nitrate (CAN) removed hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines to produce alcohols and amines in good yields. Especially, removal of the 2-hydroxyethyl ethers from C2-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C2-symmetric diols. The reactions using dual abilities of CAN, i.e.,?the ability for removal of the 2-hydroxyethyl unit and the ability for acetal hydrolysis by a single electron transfer, were also achieved successfully. The reaction conditions were very mild and efficient, and many functional groups, which can be affected under normal conditions, were unaffected during the reaction.
- Fujioka, Hiromichi,Hirose, Hideki,Ohba, Yusuke,Murai, Kenichi,Nakahara, Kenji,Kita, Yasuyuki
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p. 625 - 637
(2007/10/03)
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- A new versatile linker for the solid-phase synthesis of secondary amines
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A novel linker for the solid-phase synthesis of secondary amines based on an intramolecular cyclization was developed. The linker allows for a stepwise built-up of the secondary amines on the support. The feasibility was demonstrated in the parallel synthesis of a small set of different secondary amines.
- Glatz, Heiko,Bannwarth, Willi
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p. 149 - 152
(2007/10/03)
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- Zwitterionic rhodium complex catalyzed hydroaminomethylation of arylethylenes
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The hydroaminomethylation of arylethylenes can be achieved in high regioselectivity using the zwitterionic rhodium complex [Rh+(cod)(η6-PhBPh3)-] (1) as the catalyst under relatively mild conditions.
- Lin, Yong-Shou,El Ali, Bassam,Alper, Howard
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p. 2423 - 2425
(2007/10/03)
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- The addition of amines to diisobutylaluminum-imine complexes. Preparation of NPS R-568 hydrochloride
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A facile procedure for the preparation of secondary and tertiary amines from nitriles has been developed. The addition of amines to diisobutylaluminum-imine complexes derived by treating nitriles with DIBAL-H was found to proceed in moderate to good yield
- Barmore, Robert M.,Logan, Sarah R.,Van Wagenen, Bradford C.
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p. 3451 - 3454
(2007/10/03)
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- One-pot synthesis of secondary and tertiary amines by carbonylative hydroaminomethylation of alkenes catalyzed by di(μ-chloro)bis(η4-1,5-cyclooctadiene)dirhodium
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Secondary and tertiary amines are selectively prepared with high yields by the reaction of alkenes with primary or secondary amines, carbon monoxide and hydrogen in the presence of [Rh(cod)Cl]2 as catalyst via a one-pot hydroformylation - amine
- Rische,Eilbracht
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p. 1331 - 1337
(2007/10/03)
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- Trichlorosilane-dimethylformamide (Cl3SiH-DMF) as an efficient reducing agent. Reduction of aldehydes and imines and reductive amination of aldehydes under mild conditions using hypervalent hydridosilicates
-
Trichlorosilane-dimethylformamide (Cl3SiH-DMF) was found to be an effective reducing agent for reduction of aldehydes to alcohols, imines to amines, and also reductive amination of aldehydes. Hypervalent silicates are active species, which enable efficient reduction under mild conditions.
- Kobayashi, Shu,Yasuda, Masaru,Hachiya, Iwao
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p. 407 - 408
(2007/10/03)
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