Copper/silver-mediated direct ortho-ethynylation of unactivated (hetero)aryl C-H bonds with terminal alkyne.
A copper/silver-mediated oxidative ortho-ethynylation of unactivated aryl C-H bonds with terminal alkyne has been developed. The reaction uses the removable PIP directing group and features broad substrate scope, high functional-group tolerance, and compatibility with a wide range of heterocycles, providing an efficient synthesis of aryl alkynes. This procedure highlights the potential of copper catalysts to promote unique, synthetically enabling C-H functionalization reactions that lie outside of the current scope of precious metal catalysis.
Department of Chemistry, Zhejiang University, Hangzhou 310027 (P. R. China) http://mypage.zju.edu.cn/bfshi.
Yue-Jin
YJ
Liu
Yan-Hua
YH
Liu
Xue-Song
XS
Yin
Wen-Jia
WJ
Gu
Bing-Feng
BF
Shi
D000480:Alkynes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007700:Kinetics; D010084:Oxidation-Reduction; D012834:Silver / Q000737:chemistry*
D000480:Alkynes; D006571:Heterocyclic Compounds; D012834:Silver; D002244:Carbon; D003300:Copper; D006859:Hydrogen
CH activation; alkynylation; copper; cross-coupling; directing groups