Regioselective Fluorination of 1-(2,2-Dibromovinyl)benzene Derivatives with Wet Tetra-n-butylammonium Fluoride: One-Pot Synthesis of (Z)-1-(2-Bromo-1-fluorovinyl)benzenes

Mingzhu Zhao, Ling Ming, Jialiang Tang and Xiaoming Zhao*

*Shanghai Key Lab of Chemical Assessment and Sustainability, Department of Chemistry, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. China, Email: xmzhao08mail.tongji.edu.cn

M. Zhao, L. Ming, J. Tang, X. Zhao, Org. Lett., 2016, 18, 416-419.

DOI: 10.1021/acs.orglett.5b03448

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Abstract

A direct fluorination of 1-(2,2-dibromovinyl)benzene derivatives using wet tetra-n-butylammonium fluoride (TBAF·3H₂O) as either a base or a fluorine source provided (Z)-1-(2-bromo-1-fluorovinyl)benzene compounds in good yields with high regioselectivities.

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Key Words

fluorination

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ID: J54-Y2016