- Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers
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The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.
- Strehl, Julia,Hilt, Gerhard
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supporting information
p. 5968 - 5972
(2020/08/12)
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- Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines
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The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.
- Gudun, Kristina A.,Slamova, Ainur,Hayrapetyan, Davit,Khalimon, Andrey Y.
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supporting information
p. 4963 - 4968
(2020/04/17)
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- N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer
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A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.
- Xia, Qing,Tian, Hao,Dong, Jianyang,Qu, Yi,Li, Lili,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 9269 - 9273
(2018/06/04)
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- Pseudorotaxane orientational stereoisomerism driven by π-electron density
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Pseudo[2]rotaxane orientational isomers were formed in a stereocontrolled way by exploiting the electron-withdrawing (EW) or electron-donating (ED) effects of para-substituted dibenzylammonium axles threaded through the π-electron rich calixarene cavity, which allow the fine tuning of the weak π-π interactions.
- Gaeta, Carmine,Talotta, Carmen,Neri, Placido
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supporting information
p. 9917 - 9920
(2014/08/18)
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- Oxidative N-debenzylation of N-benzyl-N-substituted benzylamines catalyzed by horseradish peroxidase
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A report on the oxidative N-debenzylation of N-benyl-N-substituted benzylamines catalyzed by horseradish peroxidase was presented. A solution of benzylamine in benzene was added to a benzene solution of p-anisaldehyde in 100 ml flask over 10 minutes. Expulsion of proton and hydroxylation yielding α-hydroxylamines were followed by the formation of benzaldehydes and benzylamines.
- Kim, Sung Soo,Jung, Hwan
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p. 555 - 558
(2007/10/03)
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