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Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents

Author:
Yang, Chu-Ting, Zhang, Zhen-Qi, Liang, Jun, Liu, Jing-Hui, Lu, Xiao-Yu, Chen, Huan-Huan, Liu, Lei
Source:
Journal of the American Chemical Society 2012 v.134 no.27 pp. 11124-11127
ISSN:
1520-5126
Subject:
alcohols, catalytic activity, chemical bonding, chemical reactions, copper, halides
Abstract:
Practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis has been realized. The use of TMEDA and LiOMe is critical for the success of the reaction. This cross-coupling reaction occurs via an SN2 mechanism with inversion of configuration and therefore provides a general approach for the stereocontrolled formation of C–C bonds between two tertiary carbons from chiral secondary alcohols.
Agid:
5385909