Angewandte Chemie - International Edition p. 380 - 384 (2021)
Update date:2022-09-26
Topics:
Chang, Xiao-Yong
Chen, Ji-Jun
Gu, Qiang-Shuai
Jiang, Sheng-Peng
Li, Zhong-Liang
Liu, Lin
Liu, Xiao-Dong
Liu, Xin-Yuan
Su, Xiao-Long
Wang, Fu-Li
Yang, Chang-Jiang
Ye, Liu
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
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Doi:10.1080/00397911.2013.873939
(2014)Doi:10.1007/BF00475336
(1988)Doi:10.1016/S0040-4039(00)82003-1
(1988)Doi:10.1016/0040-4039(88)85189-X
(1988)Doi:10.3762/bjoc.10.81
(2014)Doi:10.1021/acs.joc.6b02106
(2016)