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Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

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Abstract

A TMSCl-mediated cascade annulation of isatin-derived propargylic alcohols for the synthesis of 2-substituted 3-chlorobenzofurans is now reported. Mechanistic investigations showed that this proceeded through a sequential Meyer–Schuster rearrangement/nucleophilic addition/intramolecular annulation. TMSCl not only acts as a promoter, but also acts as a chlorine source in this protocol.

Graphical abstract: Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

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Publication details

The article was received on 19 Jul 2018, accepted on 06 Aug 2018 and first published on 08 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01731J
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

    Z. Sun, K. Xiang, H. Tao, L. Guo and Y. Li, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01731J

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