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Issue 70, 2012
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gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes

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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.

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

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Article information


Submitted
30 May 2012
Accepted
12 Jul 2012
First published
26 Jul 2012

Chem. Commun., 2012,48, 8802-8804
Article type
Communication

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

Z. Fang, H. Yuan, Y. Liu, Z. Tong, H. Li, J. Yang, B. Barry, J. Liu, P. Liao, J. Zhang, Q. Liu and X. Bi, Chem. Commun., 2012, 48, 8802
DOI: 10.1039/C2CC33857B

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