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; Xiaoming Zhao

doi:10.1021/acs.orglett.5b03448

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

Org Lett. 2016 Feb 5;18(3):416-9. doi: 10.1021/acs.orglett.5b03448. Epub 2016 Jan 21.

Authors

Mingzhu Zhao¹, Ling Ming¹, Jialiang Tang¹, Xiaoming Zhao¹

Affiliation

¹ Shanghai Key Lab of Chemical Assessment and Sustainability, Department of Chemistry, Tongji University , 1239 Siping Road, Shanghai 200092, P. R. China.

PMID: 26793995
DOI: 10.1021/acs.orglett.5b03448

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 in toluene was accomplished, which provided (Z)-1-(2-bromo-1-fluorovinyl)benzene compounds in up to 81% yields with high regioselectivities. This reaction results strongly depend upon the reaction conditions. The mechanism of this reaction was investigated as well.

Publication types

Research Support, Non-U.S. Gov't