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

Chu-Ting Yang, Zhen-Qi Zhang, Jun Liang, Jing-Hui Liu, Xiao-Yu Lu, Huan-Huan Chen and Lei Liu*

*Tsinghua-Peking Center for Life Sciences, Department of Chemistry, Tsinghua University, Beijing 100084, China, Email: lliumail.tsinghua.edu.cn

C.-T. Yang, Z.-Q. Zhang, J. Liang, J.-H. Liu, X.-Y. Lu, H.-H. Chen, L. Liu, J. Am. Chem. Soc., 2012, 134, 11124-11127.

DOI: 10.1021/ja304848n (free Supporting Information)


Abstract

In a practical catalytic cross-coupling of secondary alkyl electrophiles with secondary alkyl nucleophiles under Cu catalysis, 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.


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Key Words

Alkanes


ID: J48-Y2012-2210