Rhodium catalyzed regioselective arene homologation of aryl urea via double C-H bond activation and migratory insertion of alkyne

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• 作者：Yan Wang ; Hao Zhou ; Ke Xu ; Mei-Hua Shen ; ^{shenmh@cczu.edu.cn} ; Hua-Dong Xu ; ^{hdxu@cczu.edu.cn}
• 关键词：Urea ; Directing group ; C&ndash ; H Activation ; Arene homologation ; Asymmetric alkynes ; Oxidative cyclization
• 刊名：Chinese Chemical Letters
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：28
• 期：1
• 页码：92-96
• 全文大小：752 K
• 卷排序：28

文摘

A convenient rhodium catalyzed oxidative arene homologation of aniline derivatives with symmetrical or unsymmetrical alkynes using Cu(OAc)2 as oxidant is described. Urea group is shown to be effective as a directing group for initial ortho C–H activation. Two migratory insertion events of alkyne into Rh–C bond occur successively, both with complete regioselectivity. This method is particularly useful for synthesis of polyarenes with different substituents, which has not been reported with conventional protocol. A mechanism has been proposed to explain the observed data.