1882-56-0Relevant 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.
Highly para-Selective C?H Alkylation of Benzene Derivatives with 2,2,2-Trifluoroethyl α-Aryl-α-Diazoesters
Ma, Ben,Chu, Zhaowei,Huang, Ben,Liu, Zhenli,Liu, Lu,Zhang, Junliang
supporting information, p. 2749 - 2753 (2017/02/26)
Compared to the most popular directing-group-assisted strategy, the “undirected” strategy for C?H bond functionalization represents a more flexible but more challenging approach. Reported herein is a gold-catalyzed highly site-selective C(sp2)?H alkylation of unactivated arenes with 2,2,2-trifluoroethyl α-aryl-α-diazoesters. This protocol demonstrates that high site-selective C?H bond functionalization can be achieved without the assistance of a directing group. In this transformation, both the gold catalyst and trifluoroethyl group on the ester of the diazo compound play vital roles for achieving the chemo- and regioselectivity.
COBALT-CATALYZED SYNTHESIS OF α-ARYLPROPIONIC AND DIARYLACETIC ACIDS
Francalanci, F.,Gardano, A.,Foa, M.
, p. 277 - 282 (2007/10/02)
The cobalt-catalyzed carbonylation of ArCH(R)X (R=CH3, C6H5; X=Cl, Br) in alcoholic solvents under atmospheric pressure of CO is reported.Selective, high yield synthesis of the corresponding acids ArCH(R)COOH can be achieved within a very narrow range of experimental conditions by controlling kinetically the reversible interconversion of intermediate aryl and alkylcobalt complexes.The important roles of the base and of the alcoholic medium are briefly discussed.