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Synthesis of Benzo[b]thiophenes via Electrophilic Sulfur Mediated Cyclization of Alkynylthioanisoles

Zahra Alikhani, Alyssa G. Albertson, Christopher A. Walter, Prerna J. Masih and Tanay Kesharwani*

*Department of Chemistry, University of West Florida, 11000 University Pkwy, Pensacola, Florida 32514, United States, Email:

Z. Alikhani, A. G. Albertson, C. A. Walter, P. J. Masih, T. Kesharwani, J. Org. Chem., 2022, 87, 6312-6320.

DOI: 10.1021/acs.joc.1c02606

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The use of a stable dimethyl(thiodimethyl)sulfonium tetrafluoroborate salt enables an electrophilic cyclization o-alkynyl thioanisoles to provide 2,3-disubstituted benzo[b]thiophenes with a valuable thiomethyl group at position 3 in excellent yields. The reaction utilizes moderate reaction conditions while tolerating various functionalities.

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proposed mechanism

Key Words


ID: J42-Y2022