Alkane C-H Insertion by Aryne Intermediates with a Silver Catalyst

作者:Yun Sang Young; Wang Kung Pern; Lee Nam Kyu; Mamidipalli Phani; Lee Daesung*
来源:Journal of the American Chemical Society, 2013, 135(12): 4668-4671.
DOI:10.1021/ja400477r

摘要

Arynes generated directly from alkyne building blocks in the presence of silver catalysts effectively activate primary, secondary, and tertiary alkane C-H bonds. This C-H insertion requires only a catalytic amount of silver complex and modest heating compared to harsh conditions and extra promoters including directing groups, oxidants, and bases in typical transition-metal-based C-H bond functionalizations. Preliminary mechanistic studies suggest that the C-H bond-breaking and new bond-forming events take place in a concerted manner, rendering a formal 1,2-addition of C-H bond across the pi-bond of arynes.

  • 出版日期2013-3-27