- AgOAc-catalyzed aldehyde allylation using allyldimethyl(2-pyridyl)silane
-
Silver salts having relatively strong Ag-O bond were found to promote the allylation of aldehydes with allyldimethyl(2-pyridyl)silane. Catalytic allylation is also possible when AgOAc was employed. A novel cooperative activation of allyl(2-pyridyl)silane has been implicated from several control experiments.
- Itami, Kenichiro,Kamei, Toshiyuki,Mineno, Masahiro,Yoshida, Jun-Ichi
-
-
Read Online
- Bismuth(III) Chloride-Aluminium-promoted Allylation of Aldehydes to Homoallylic Alcohols in Aqueous Solvent
-
In the presence of bismuth(III)chloride-metallic aluminium, allylic halides have been found to react with aldehydes at room temperature in tetrahydrofuran-water to afford the corresponding homoallylic alcohols in high yields.
- Wada, Makoto,Ohki, Hidenori,Akiba, Kin-ya
-
-
Read Online
- Aerosol-spraying synthesis of periodic mesoporous organometalsilica spheres with chamber cavities as active and reusable catalysts in aqueous organic reactions
-
Organometal-bridged periodic mesoporous catalysts with uniform spheres containing cavities in chambers were synthesized by rapid aerosol-spray assisted co-condensation between organometallic silane and tetraethoxysilane (TEOS) in the presence of cetyltrimethyl ammonium bromide (CTAB) and NaCl double templates. The as-prepared M-PPh2-PMO(H) catalysts (M = Pd 2+, Rh+ and Ru2+) were used in various water-medium organic reactions with the aim of diminishing environmental pollution from organic solvents. These catalysts exhibited high catalytic activities and selectivities owing to the high surface area, the uniform distribution of active sites, the ordered mesoporous channels and especially, the cavities as microreactors which facilitated the diffusion and adsorption of organic reactants. Meanwhile, they also displayed strong durability and could be used repeatedly owing to the organometals incorporated into silica walls and the presence of chamber cavities which could effectively protect the ordered mesoporous structure from damage and also inhibit the leaching of active sites.
- Zhang, Fang,Kang, Chunmei,Wei, Yongyi,Li, Hexing
-
-
Read Online
- Lanthanide(II) Iodide Catalysed Photochemical Allylation of Aldehydes with Allylic Halides
-
Lanthanide(II) iodides such as SmI2 and YbI2 show high catalytic activity for the photochemical allylation of aldehydes with allylic halides to give the corresponding homoallylic alcohols.
- Kondo, Teruyuki,Akazome, Motohiro,Watanabe, Yoshihisa
-
-
Read Online
- Periodic mesoporous organosilica grafted palladium organometallic complex: Efficient heterogeneous catalyst for water-medium organic reactions
-
Water-medium organic reactions were studied over periodic mesoporous silica (PMO) containing Pd(II) organometallic complex. This heterogeneous catalyst was achieved by Pd(II) compound coordinated with the PPh2-ligand onto the pore surface of ph
- Huang, Jianlin,Zhang, Fang
-
-
Read Online
- Indium(I)/CuFe2O4 Reagent for Allylation of Carbonyls and Epoxide Rearranged Carbonyls
-
Abstract: Indium(I)/CuFe2O4 reagent forcarbonyl allylation and epoxide rearranged carbonyl allylation is proposed forformation of homoallylic alcohols. The In(I) reagent in combination withcatalytic amount of CuFe2O4support in situ formation of nucleophilicallylic indium from allyl halide in THF medium. Nucleophilic allylic indiumspecies react with carbonyls to form homoallyl alcohols in good to excellentyields. Under the presented reaction conditions arylepoxides undergo smoothrearrangement into aldehydes that are also allylated with formation of homoallylalcohols. The process is highly efficient and tolerates different functionalgroups.
- Kundu, M.,Mandal, S. P.,Mondal, B.,Roy, U. K.
-
-
Read Online
- Barbier-type addition of alkyl halides to aldehydes promoted by pentacarbonyliron
-
The yield and structure of products of the Barbier-type addition of alkyl halides (perfluorobutyl iodide, allyl bromide, allyl iodide, and hexyl iodide) to para-substituted benzaldehydes in the presence of pentacarbonyliron are essentially determined, on the one hand, by the ability of alkyl halide to be reduced to carbanion and, on the other, by the electrophilicity of the aldehyde reaction center which in turn depends on the nature of para-substituent in the aromatic ring.
- Vasil'Eva,Mysova,Chakhovskaya,Terent'Ev
-
-
Read Online
- A novel indium-boron amorphous alloy mediator for barbier-type carbonyl allylation in aqueous medium
-
A novel indium-boron (In-B) amorphous alloy was prepared by chemical reduction of indi- um(III) ions [In3+] with borohydride [BH 4-] in aqueous solution and was applied to the water-medium Barbier-type allylation reactions
- Li, Hui,Dong, Fuxing,Xiong, Mingwen,Li, Hexing,Li, Ping,Zhou, Xinggui
-
-
Read Online
- Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
-
A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
- Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
-
supporting information
p. 574 - 580
(2021/11/13)
-
- Nitrogen-Doped Carbon-Incarcerated Zinc Electrodes as Heterogeneous Catalysts for Electrochemical Allylation of Carbonyl Compounds
-
Electrochemical allylation reactions of carbonyl compounds using cathodes prepared from nitrogen-doped carbon (NDC)-incarcerated zinc catalysts have been developed. A range of aldehydes and ketones afforded the desired allylic alcohols in high yields with 10 mol % zinc leaching, and the heterogeneous nature of the active species was suggested. Compared with bulk zinc electrodes, NDC-stabilized zinc nanoparticle species were compatible with a broader range of heteroaromatic substrates and enabled the use of an undivided cell.
- Masuda, Ryusuke,Yasukawa, Tomohiro,Yamashita, Yasuhiro,Kobayashi, Shū
-
p. 3453 - 3460
(2022/02/23)
-
- A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes
-
Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to 98% ee). Meanwhile, the NHK vinylation of aldehydes produce desired allylic alcohols in satisfactory yields (up to 88%) and a high level of enantioselectivity (up to 97% ee). We developed a reliable and milder protocol for preparing chiral homoallylic and allylic alcohols.
- Chen, Chinpiao,Kumbhar, Sharad V.
-
-
- Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex
-
The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2-phenylpyridine, 2 mol %), and N,N-diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. (Figure presented.).
- Gualandi, Andrea,Rodeghiero, Giacomo,Perciaccante, Rossana,Jansen, Thomas Paul,Moreno-Cabrerizo, Cristina,Foucher, Charles,Marchini, Marianna,Ceroni, Paola,Cozzi, Pier Giorgio
-
supporting information
p. 1105 - 1111
(2021/01/04)
-
- Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates
-
Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.
- Suzuki, Hiroyuki,Yamaguchi,Itoh, Akichika
-
p. 1489 - 1494
(2020/12/13)
-
- Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes
-
The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.
- Shi, Caizhe,Li, Fusheng,Chen, Yuqing,Lin, Shuangjie,Hao, Erjun,Guo, Zhuowen,Wosqa, Urwa Tul,Zhang, Dandan,Shi, Lei
-
p. 2992 - 2998
(2021/03/09)
-
- Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand-Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy
-
Transient receptor potential ankyrin 1 (TRPA1) is a nonselective calcium-permeable ion channel highly expressed in the primary sensory neurons functioning as a polymodal sensor for exogenous and endogenous stimuli and has generated widespread interest as a target for inhibition due to its implication in neuropathic pain and respiratory disease. Herein, we describe the optimization of a series of potent, selective, and orally bioavailable TRPA1 small molecule antagonists, leading to the discovery of a novel tetrahydrofuran-based linker. Given the balance of physicochemical properties and strong in vivo target engagement in a rat AITC-induced pain assay, compound 20 was progressed into a guinea pig ovalbumin asthma model where it exhibited significant dose-dependent reduction of inflammatory response. Furthermore, the structure of the TRPA1 channel bound to compound 21 was determined via cryogenic electron microscopy to a resolution of 3 ?, revealing the binding site and mechanism of action for this class of antagonists.
- Terrett, Jack A.,Chen, Huifen,Shore, Daniel G.,Villemure, Elisia,Larouche-Gauthier, Robin,Déry, Martin,Beaumier, Francis,Constantineau-Forget, Léa,Grand-Ma?tre, Chantal,Lépissier, Luce,Ciblat, Stéphane,Sturino, Claudio,Chen, Yong,Hu, Baihua,Lu, Aijun,Wang, Yunli,Cridland, Andrew P.,Ward, Stuart I.,Hackos, David H.,Reese, Rebecca M.,Shields, Shannon D.,Chen, Jun,Balestrini, Alessia,Riol-Blanco, Lorena,Lee, Wyne P.,Liu, John,Suto, Eric,Wu, Xiumin,Zhang, Juan,Ly, Justin Q.,La, Hank,Johnson, Kevin,Baumgardner, Matt,Chou, Kang-Jye,Rohou, Alexis,Rougé, Lionel,Safina, Brian S.,Magnuson, Steven,Volgraf, Matthew
-
p. 3843 - 3869
(2021/05/04)
-
- Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions
-
Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.
- Potenti, Simone,Gualandi, Andrea,Puggioli, Alessio,Fermi, Andrea,Bergamini, Giacomo,Cozzi, Pier Giorgio
-
supporting information
p. 1624 - 1627
(2021/02/05)
-
- Allylation and propargylation of aldehydes mediated byin situgenerated zinc from the redox couple of Al and ZnCl2in 2N HCl
-
A simple one pot allylation and propargylation of aldehydes mediated by zinc(0), which isin situgenerated from the redox couple of Al and ZnCl2in 2N HCl, is demonstrated to afford the corresponding homoallyl and homopropargyl alcohols with exce
- Mondal, Bibhas,Adhikari, Utpal,Hajra, Partha Pratim,Roy, Ujjal Kanti
-
p. 7163 - 7173
(2021/05/03)
-
- Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes
-
Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u
- Chen, Mingjie,Li, Wenbo,Wang, Lei,Wang, Yuzhuo,Zhang, Junliang,Zhang, Kenan
-
supporting information
p. 4421 - 4427
(2020/02/11)
-
- 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
-
This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.
- Benaglia, Maurizio,Benincori, Tiziana,Raimondi, Laura Maria,Rossi, Sergio
-
p. 535 - 546
(2020/03/27)
-
- Production method of 1-(4-chlorophenyl)-3-buten-1-ol
-
The invention relates to a production method of 1-(4-chlorophenyl)-3-buten-1-ol. The method comprises the following multiple steps: adding water, crushed p-chlorobenzaldehyde and a catalyst into a reaction kettle, performing fast stirring, dropwise adding
- -
-
Paragraph 0028-0045
(2020/01/12)
-
- Copper-Impregnated Magnesium-Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
-
Copper-impregnated magnesium-lanthanum mixed oxide [Cu(II)/Mg?La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application
- Laha, Soumi,Likhar, Pravin R.,Pogula, Jaya,Sreedhar, B.
-
supporting information
(2020/02/11)
-
- Cp2TiCl2-Catalyzed Photoredox Allylation of Aldehydes with Visible Light
-
A Barbier-type Cp2TiCl2-mediated (10 mol %) photoredox allylation of aldehydes under irradiation with visible light (blue light-emitting diodes (LEDs), 450 nm) and in the presence of an organic dye (3DPAFIPN, 5 mol %) with allylbromides is described.
- Bergamini, Giacomo,Calogero, Francesco,Cozzi, Pier Giorgio,Fermi, Andrea,Gualandi, Andrea,Guazzi, Simone,Mazzarini, Martino
-
p. 3857 - 3863
(2020/03/26)
-
- A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
-
A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re
- Yin, JieXiang,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
-
p. 2347 - 2354
(2020/02/04)
-
- Axially chiral N,N′-dioxides ethers for catalysis in enantioselective allylation of aldehydes
-
A series of axially chiral ethers synthesized from biscarboline N,N′-dioxides, (S)-1a to (S)-1n, was investigated in enantioselectivity addition reactions of allyltrichlorosilane with a series of substituted aldehydes, including bulky substituted aldehydes. High enantioselectivities (up to 96%ee) were achieved using the catalyst (S)-1k at 1 mol % loading.
- Wu, Shijie,Xing, Yongfei,Wang, Jie,Guo, Xingchen,Zhu, Huajie,Li, Wan
-
supporting information
p. 947 - 957
(2019/08/30)
-
- Hollow organic polymeric nano-bowls-supported BINOL-derived chiral phosphoric acid: enhanced catalytic performances in the enantioselective allylation of aromatic aldehydes
-
To improve the catalytic efficiency of expensive and versatile 1, 1′-binaphthol-derived chiral phosphoric acid with 2, 4, 6-tris(isopropyl)phenyl substituents and mass transfer of reactants in heterogeneous catalysis, a hollow organic polymeric nano-bowl
- Yan, Zhengwei,Xie, Guangxin,Zhang, Jianing,Ma, Xuebing
-
-
- Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones via Chemoenzymatic Sequential DKR-RCM Reaction
-
The enantiomerically pure 5,6-dihydropyran-2-ones play a crucial role as the building blocks in the synthesis of various bioactive compounds. A new straightforward protocol toward enantiomerically pure 5,6-dihydropyran-2-ones based on enzymatic dynamic ki
- Koszelewski, Dominik,Borys, Filip,Brodzka, Anna,Ostaszewski, Ryszard
-
supporting information
p. 1653 - 1658
(2019/01/24)
-
- Allylation of aldehydes by dual photoredox and nickel catalysis
-
Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(ii) complex, [Ru(bpy)3]2+ as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.
- Gualandi, Andrea,Rodeghiero, Giacomo,Faraone, Adriana,Patuzzo, Filippo,Marchini, Marianna,Calogero, Francesco,Perciaccante, Rossana,Jansen, Thomas Paul,Ceroni, Paola,Cozzi, Pier Giorgio
-
supporting information
p. 6838 - 6841
(2019/06/18)
-
- OXADIAZOLE TRANSIENT RECEPTOR POTENTIAL CHANNEL INHIBITORS
-
The invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof wherein A, X, R1, R4 and n are as defined herein. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.
- -
-
-
- TetraPh-Tol-BITIOPO: A new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions
-
A new chiral phosphine oxide based on a 3,3′-bithiophene scaffold (TetraPh-Tol-BITIOPO) was synthesized, fully characterized and separated into antipodes through chiral HPLC. This new compound was successfully employed as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions involving trichlorosilyl compounds. The new atropisomeric catalyst was able to promote the allylation of aldehydes with allyltrichlorosilane in up to 98% yield and up to 96% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones and β-hydroxy thioesters, with good chemical yields and modest stereochemical efficiency. Computational studies helped to elucidate and to rationalize the stereochemical outcome of the reactions catalyzed by TetraPh-Tol-BITIOPO that was found to favour the formation of the isomer with an opposite absolute configuration in comparison with the products obtained with the previously reported 3,3′-bithiophene-based catalyst.
- Mirco, Abbinante Vincenzo,Maurizio, Benaglia,Sergio, Rossi,Tiziana, Benincori,Roberto, Cirilli,Marco, Pierini
-
supporting information
p. 7474 - 7481
(2019/08/20)
-
- Cationic Cobalt Porphyrin-Catalyzed Allylation of Aldehydes with Allyltrimethylsilanes
-
Cationic cobalt porphyrin-catalyzed allylation of aldehydes with allyltrimethylsilanes is developed. The formation of the aldehyde-cobalt porphyrin complex, the key intermediate for the addition of allylsilanes, is confirmed by theoretical studies and syn
- Tomifuji, Rei,Masuda, Shota,Kurahashi, Takuya,Matsubara, Seijiro
-
p. 3834 - 3837
(2019/05/24)
-
- Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions
-
We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compou
- Chatterjee, Rana,Samanta, Satyajit,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
-
supporting information
p. 276 - 283
(2019/01/04)
-
- Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water
-
Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].
- Sawkmie, Micky Lanster,Paul, Dipankar,Khatua, Snehadrinarayan,Chatterjee, Paresh Nath
-
-
- Synthesis and characterization of nano?zinc wire using a self designed unit galvanic cell in aqueous medium and its reactivity in propargylation of aldehydes
-
Electrochemistry is used for propargylation of carbonyls in aqueous ZnCl2 medium. For electrochemical process we designed a unit galvanic cell. ZnCl2 is used as stoichiometric reagent and causes electrochemical deposition of zinc in
- Mondal, Bibhas,Mandal, Siba Prasad,Kundu, Mousumi,Adhikari,Roy, Ujjal Kanti
-
supporting information
p. 4669 - 4675
(2019/07/22)
-
- Chiral Bisdiphenylphosphine Dioxides Bearing a Bis(triazolyl) Backbone as Promising Lewis Bases for Asymmetric Organocatalysis
-
Two chiral C2-symmetric diphenylphosphine dioxides bearing an original bis(triazolyl) backbone were prepared starting from inexpensive and readily available precursors. The key step involves the simultaneous formation of five bonds in one chemi
- Sevrain, Nicolas,Volle, Jean-Noel,Pirat, Jean-Luc,Ayad, Tahar,Virieux, David
-
supporting information
p. 2267 - 2272
(2018/06/04)
-
- Axial-Chiral Biisoquinoline N, N′-Dioxides Bearing Polar Aromatic C-H Bonds as Catalysts in Sakurai-Hosomi-Denmark Allylation
-
The design, synthesis, and evaluation of axial-chiral biisoquinolines bearing polar aromatic C-H bonds as Lewis base catalysts are reported. Lewis bases containing the 3,5-bis(trifluoromethyl)phenyl group were found to be significantly more enantioselecti
- Reep, Carlyn,Morgante, Pierpaolo,Peverati, Roberto,Takenaka, Norito
-
supporting information
p. 5757 - 5761
(2018/09/29)
-
- Synthetic Studies Towards the Synthesis of 6-Substituted 3-Fluoro-5,6-dihydropyran-2-ones 1
-
The synthesis of 6-substituted 3-fluoro-5,6-dihydropyran-2-ones under mild conditions is described. The key step of the synthesis involves a Julia-Kocienski olefination.
- Mandal, Samir K.,Sarkar, Apurba,Chakraborty, Puskin,Chattopadhyay, Ashoke P.
-
supporting information
p. 75 - 78
(2017/10/06)
-
- [bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
-
Barbier-type allylation reactions of aldehydes and ketones have been carried out with both unsubstituted and γ-substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br], but not in H2O, organic solvents, or
- Dey, Papiya,Koli, Mrunesh,Goswami, Dibakar,Sharma, Anubha,Chattopadhyay, Subrata
-
p. 1333 - 1341
(2018/04/02)
-
- Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes
-
A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications.
- Becerra-Figueroa, Liliana,Tiniakos, Alexander F.,Prunet, Jo?lle,Gamba-Sánchez, Diego
-
supporting information
p. 6929 - 6932
(2018/11/25)
-
- Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC
-
The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.
- Tang, Jian,Lin, Yuzhou,Yang, Bo,Zhou, Jie,Tang, Weihua
-
p. 566 - 573
(2017/08/26)
-
- Heteropoly Acid Supported on Silica Gel as Catalyst for the Asymmetric Transfer Allylation of Aromatic Aldehydes under Solvent-Free Conditions
-
A new convenient method for the asymmetric transfer allylation of aromatic aldehydes was developed. The reaction gave the best results using a chiral allyl donor molecule derived from (-)-menthone in the presence of heteropoly acids supported on silica gel under solvent-free conditions, and the desired homoallylic alcohol derivatives were obtained in good yields with good to high enantioselectivity.
- Nunokawa, Shiori,Oki, Kazuya,Yamashita, Keisuke,Okuyama, Atsushi,Ueda, Tadaharu,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
-
supporting information
p. 597 - 600
(2017/03/11)
-
- Novel chiral bis-phosphoramides as organocatalysts for tetrachlorosilane-mediated reactions
-
The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/pri
- Rossi, Sergio,Ziliani, Marco,Annunziata, Rita,Benaglia, Maurizio
-
supporting information
(2018/01/12)
-
- An organoantimony complex with intramolecular N?→?Sb coordination as effective and recyclable catalyst for the allylation of aldehydes with tetraallyltin
-
An air-stable hypervalent organoantimony (III) triflate complex (PhN(CH2C6H4)2SbOSO2CF3) having intramolecular N?→?Sb coordination was synthesized and characterized by techniques such as s
- Tan, Nianyuan,Nie, Tong,Au, Chak-Tong,Lan, Donghui,Wu, Shuisheng,Yi, Bing
-
supporting information
p. 2592 - 2595
(2017/06/13)
-
- Palladacycles having normal and spiro chelate rings designed from bi- and tridentate ligands with an indole core: Structure, synthesis and applications as catalysts
-
1-Pyridin-2-ylmethyl-1H-indole-3-carbaldehyde and 1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1H-indole-3-carbaldehyde were synthesized. Their condensation with benzyl amine resulted in indole core containing Schiff bases benzyl-(1-pyridin-2-ylmethyl-1H-in
- Singh, Mahabir P.,Saleem, Fariha,Pal, Ram S.,Singh, Ajai K.
-
p. 11342 - 11352
(2017/10/05)
-
- Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction
-
A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yiel
- Becerra-Figueroa, Liliana,Brun, Elodie,Mathieson, Michael,Farrugia, Louis J.,Wilson, Claire,Prunet, Jo?lle,Gamba-Sánchez, Diego
-
supporting information
p. 301 - 305
(2017/01/13)
-
- Green Organocatalytic Dihydroxylation of Alkenes
-
An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.
- Theodorou, Alexis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
-
p. 1502 - 1509
(2017/04/01)
-
- Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
-
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
- Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
-
supporting information
p. 2056 - 2059
(2017/02/15)
-
- Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
-
Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction con
- Mondal, Keshab,Pan, Subhas Chandra
-
supporting information
p. 534 - 537
(2017/02/05)
-
- Polystyrene-Supported TRIP: A highly recyclable catalyst for batch and flow enantioselective allylation of aldehydes
-
The widely applicable TRIP phosphoric acid catalyst has been immobilized on polystyrene using a copolymerization-based strategy. The resin (PS-TRIP) has proven to be highly active and enantioselective in the asymmetric allylboration of aldehydes. Moreover
- Clot-Almenara, Lidia,Rodríguez-Escrich, Carles,Osorio-Planes, Laura,Pericas, Miquel A.
-
p. 7647 - 7651
(2018/05/23)
-
- Ter-pyridine catalyzed allylation of aldehydes and ketones under metal-free condition
-
Ter-pyridine derivatives were found to be potential catalyst for homoallylation of carbonyl groups. High yields of the products with short reaction times of ~2 h were observed in several cases. These new catalysts work efficiently with the simple reagent such as allyl magnesium bromide and hence can avoid the use of other sensitive or toxic reagents. It was found that the presence of polar groups on the catalysts made them extremely efficient without the presence of any metal salts.
- Datilus, Vicklyn,Abdulkarim, Mary,Patrizio, Andrew,Kaur, Parminder
-
supporting information
p. 2778 - 2781
(2016/06/09)
-
- A Green approach for allylations of aldehydes and ketones: Combining allylborate, mechanochemistry and lanthanide catalyst
-
Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles.
- De Souza, Viviane P.,Oliveira, Cristiane K.,De Souza, Thiago M.,Menezes, Paulo H.,Alves, Severino,Longo, Ricardo L.,Malvestiti, Ivani
-
-
- A Mild, efficient protocol for the synthesis of homoallylic alcohols using potassium allyltrifluoroborate promoted by salicylic acid
-
Background: In the current decade, organotrifluoroborates have attained remarkable development in Chemistry and Materials. This can be evidenced by the increasing number of articles, review articles and patents devoted to this subject. As a consequence, the number of citations derived from papers dealing with this subject has experienced an exponential growth in the last years. The aim of this paper to describe a methodology based on the use of potassium allyltrifluoroborate for the synthesis of homoallylic alcohols using water as a co-solvent and under mild reaction conditions. Methods: The methodology is very robust (wide range of aldehydes) and simple, it uses low catalyst loadings and it is synthetically useful because it could be applied for the synthesis of more complex compounds. In addition, detailed experimental procedures, including the preparation of the starting materials, as well as the corresponding 1H, 13C, 19F and 11B spectra for all synthesized compounds are provided. Results: The method is environmentally friendly while it uses water as a solvent and the desired compounds containing different functionalities were obtained in moderate to good yields (60-93%) without the need of further purification in a very chemo- and regioselective way. Conclusion: Salicylic acid can efficiently promote the allylation of aldehydes using potassium allyltrifluoroborate at room temperature to yield the corresponding homoallylic alcohols in moderate to good yields. The method is efficient and environmentally friendly while it uses water as co-solvent. In addition the method is regio- and chemoselective and could be applied in the synthesis of more complex homoallylic alcohols.
- Silva, Jadson F.,Lima, Josefa A.C.,De Freitas, Jucleiton J.R.,Freitas, Ladjane P.S.R.,Menezes, Paulo H.,Freitas, Juliano C.R.
-
-
- A ionic the bistriphenyl make PVC possess enough preparation and application of (V) complex
-
The invention provides a preparation method of an ionic type bis-triphenyl organic antimony (V) complex and a method for synthesizing allyl alcohol compounds under catalysis of the ionic type bis-triphenyl organic antimony (V) complex. The complex is a cationic type organic antimony complex, wherein two antimony atoms in the complex are bridged by virtue of oxygen atoms and are pentavalent; and each antimony atom is in coordination with one water molecule, and an ionic bond is formed by the entire organic antimony cationic part with corresponding anions. The synthetic method comprises the following step: by taking the bis-triphenyl organic antimony (V) complex as a catalyst, taking a commonly-used organic solvent as a reaction solvent, and taking aldehyde and tetraallyltin as raw materials, performing reaction. The synthetic method can be used for providing a novel low-cost and 'green' route for preparing the allyl alcohol compounds, and has the advantages that target product selectivity and yield are high, the catalyst can be repeatedly used, corresponding ketone can be obtained by performing simple column chromatography separation on the product, and the whole reaction and separation process is simple to operate and is green and environment-friendly.
- -
-
Paragraph 0060; 0061
(2017/01/02)
-
- Palladacycles of unsymmetrical (N,C-,E) (E = S/Se) pincers based on indole: Their synthesis, structure and application in the catalysis of Heck coupling and allylation of aldehydes
-
Unsymmetrical (N,C,E)-type pincer ligand precursors [L1 and L2: E = S/Se] with an indole core were synthesized for the first time by the condensation of 1-(2-phenylsulfanyl/selenylethyl)-1H-indole-3-carbaldehyde with benzyl amine. The synthetic protocols
- Singh, Mahabir P.,Saleem, Fariha,Rao, Gyandshwar K.,Kumar,Joshi, Hemant,Singh, Ajai K.
-
p. 6718 - 6725
(2016/05/09)
-
- Facile access to zinc and cadmium selones: Highly active catalysts for Barbier reactions in aqueous media
-
The syntheses and structures of five mononuclear zinc and cadmium selone complexes along with a polynuclear cadmium selone 1D chain were described. The mononuclear homoleptic zinc selone complexes were the first examples of structurally characterized zinc
- Babu, Chatla Naga,Srinivas, Katam,Prabusankar, Ganesan
-
p. 6456 - 6465
(2016/05/09)
-
- Mild bottom-up synthesis of indium(0) nanoparticles: Characterization and application in the allylation of carbonyl compounds
-
Very reactive, monodisperse (4.0 ± 0.5 nm) spherical indium(0) nanoparticles have been generated in situ, in a simple, mild and efficient way, by fast reduction of commercially available indium(iii) chloride with lithium sand and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) in THF, at room temperature, and in the absence of any anti-agglomeration additives or ligands. The as-synthesized bare InNPs were applied for the allylation of a variety of aldehydes and ketones. For most of the compounds tested, the corresponding homoallylic alcohols were obtained as the major product in good to excellent yield.
- Dorn, Viviana,Chopa, Alicia,Radivoy, Gabriel
-
p. 23798 - 23803
(2016/03/12)
-
- Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes
-
An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi
- Mondal, Keshab,Mondal, Buddhadeb,Pan, Subhas Chandra
-
p. 4835 - 4840
(2016/07/06)
-
- Waste management in zinc promoted allylation of aldehyde
-
By using an efficient, sustainable and green procedure, the waste zinc material in Zn(0) promoted Grignard-Barbier type allylation of aldehydes has been successfully utilized as a reusable material for the adsorption of various dyes and also converted int
- Pratihar, Sanjay,Kakoty, Anindita,Sarmah, Kasturi
-
p. 5347 - 5356
(2016/07/06)
-