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Issue 9, 2016
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Silver-mediated oxidative annulation of N-arylthio succinimides with alkynes: direct access to benzo[b]thiophenes

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Abstract

A convenient synthetic route to 2,3-diarylbenzo[b]thiophene derivatives via Ag-catalyzed intermolecular oxidative cyclization between bench-stable N-arylthio succinimides and unactivated internal alkynes is demonstrated herein. The reaction indicates a broad scope, facilitating the construction of diverse arrays of π-conjugated 2,3-diaryl substituted benzothiophenes. The method involves oxidative cleavage of the S–N bond and annulation of alkynes with the concurrent 1,2-S-migration to yield benzo[b]thiophenes.

Graphical abstract: Silver-mediated oxidative annulation of N-arylthio succinimides with alkynes: direct access to benzo[b]thiophenes

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Supplementary files

Article information


Submitted
10 Jun 2016
Accepted
15 Jul 2016
First published
25 Jul 2016

Org. Chem. Front., 2016,3, 1126-1130
Article type
Research Article

Silver-mediated oxidative annulation of N-arylthio succinimides with alkynes: direct access to benzo[b]thiophenes

E. Ramesh, M. Shankar, S. Dana and A. K. Sahoo, Org. Chem. Front., 2016, 3, 1126 DOI: 10.1039/C6QO00259E

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