gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes

Zhongxue Fang; Haiyan Yuan; Ying Liu; Zixun Tong; Huiqin Li; Jin Yang; Badru-Deen Barry; Jianquan Liu; Peiqiu Liao; Jingping Zhang; Qun Liu; Xihe Bi

doi:10.1039/C2CC33857B

gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes†

Zhongxue Fang,^a Haiyan Yuan,^a Ying Liu,^a Zixun Tong,^a Huiqin Li,^a Jin Yang,^a Badru-Deen Barry,^a Jianquan Liu,^a Peiqiu Liao,^a Jingping Zhang,*^a Qun Liu*^a and Xihe Bi*^ab

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* Corresponding authors

^a Department of Chemistry, Northeast Normal University, Changchun 130024, China
E-mail: bixh507@nenu.edu.cn, liuqun@nenu.edu.cn, zhangjingping66@yahoo.cn

^b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Abstract

gem-Dialkylthio vinylallenes were obtained for the first time and applied to the divergent synthesis of fully-substituted pyrroles and thiophenes by domino cyclizations. These two cyclization pathways were regulated by alkylthio groups. Plausible reaction mechanisms were presented and supported by DFT calculations. An unprecedented metal-free carbothiolation was discovered in the formation of thiophenes.

Chemical Communications

gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes†

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gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes

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