Synthesis of Bifunctional Thiophenes via Fiesselmann Condensation of Ynone Trifluoroborate Salts

Prisca Fricero, Laurent Bialy, Werngard Czechtizky, María Méndez and Joseph P. A. Harrity*

*Department of Chemistry, University of Sheffield, Brook Hill, S3 7HF, U.K., Email: j.harritysheffield.ac.uk

P. Fricaro, L. Bialy, W. Czechtizky, M. Méndez, J. P. A. Harrity, Org. Lett., 2018, 20, 198-200.

DOI: 10.1021/acs.orglett.7b03558

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Abstract

Ynone trifluoroborate salts undergo a base-promoted condensation reaction with alkylthiols to provide thiophene trifluoroborates in high yield with complete regiocontrol.

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proposed mechanism

functionalization reactions

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Key Words

thiophenes

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ID: J54-Y2018