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

Literature Information

Publication Date 2018-08-08
DOI 10.1039/C8OB01731J
Impact Factor 3.876
Authors

Zhou Sun, Kuirong Xiang, Hua Tao, Liqun Guo, Ying Li


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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.

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Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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