92548-88-4Relevant articles and documents
Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts
Liao, Li-Li,Cao, Guang-Mei,Ye, Jian-Heng,Sun, Guo-Quan,Zhou, Wen-Jun,Gui, Yong-Yuan,Yan, Si-Shun,Shen, Guo,Yu, Da-Gang
, p. 17338 - 17342 (2019/01/04)
Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.
Reactions of 1-tert-Butyl-3-phenylaziridinone and α-Bromo-N-tert-butylphenylacetamide with Benzyl-Grignard Reagents
Baumgarten, Henry E.,Chiang, Nein-Chu Robert,Elia, Victor J.,Beum, Paul V.
, p. 5507 - 5512 (2007/10/02)
1-tert-Butyl-3-phenylaziridinone (1) reacts with benzyl halide Grignard reagents (Br and Cl) to give N-tert-butyl-2,3-diphenylpropanamide (4), N-tert-butyl-2-phenylacetamide (3), N-tert-butyl-2-o-tolyl-2-phenylacetamide (5), 1-(tert-butylamino)-1,3-diphenylpropan-2-one (7), N-benzyl-N-tert-butyl-2-phenylacetamide (6), and N-tert-butyl-2-halo-2-phenylacetamide (2, X = Br, Cl).The choice of solvent appears to determine the relative amounts of products 4 and 5.The bromo amide 2 reacts with the Grignard reagent to give 3, 4, 5, 6, and 7 and may be involved to some extentin the reaction of 1 with benzyl-Grignard reagents.The formation of 5 represents anew type of "abnormal" product from a reaction of the benzyl-Grignard reagent; however, this product appears to fit well into the mechanistic pattern established for prior examples.