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铜催化的1,n-烯炔与α-羰基烷基溴通过C-Br/C-H官能化的氧化[2+2+1]环化反应。

Copper-catalyzed oxidative [2+2+1] annulation of 1,n-enynes with α-carbonyl alkyl bromides through C-Br/C-H functionalization.

作者信息

Hu Ming, Song Ren-Jie, Ouyang Xuan-Hui, Tan Fang-Lin, Wei Wen-Ting, Li Jin-Heng

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.

出版信息

Chem Commun (Camb). 2016 Feb 25;52(16):3328-31. doi: 10.1039/c5cc10132h.

Abstract

The Cu-catalyzed oxidative [2+2+1] annulation of 1,n-enynes (n = 6, 7) with α-carbonyl alkyl bromides through C-Br/C-H functionalization has been developed. Using Ag2CO3/tert-butyl hydroperoxide (TBHP) as co-oxidants, α-carbonyl alkyl bromides provide two bonds, the α-C(sp(3))-Br bonds and the α-C(sp(3))-H bonds, to cyclize with the 1,n-enynes and Cu(MeCN)4PF6, thus forming three new C-C bonds and two rings in a single reaction.

摘要

已开发出通过C-Br/C-H官能团化实现的铜催化1,n-烯炔(n = 6, 7)与α-羰基烷基溴的氧化[2+2+1]环化反应。使用碳酸银/叔丁基过氧化氢(TBHP)作为共氧化剂,α-羰基烷基溴提供两个键,即α-C(sp(3))-Br键和α-C(sp(3))-H键,与1,n-烯炔和四氟硼酸四甲基铜(II)发生环化反应,从而在单一反应中形成三个新的C-C键和两个环。

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