Palladium-catalyzed cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene

Abstract

α-Trifluoromethyl alkenes can be used as peptide isosteres, moreover, the pre-installed vinyl group make it possible that transformation to diverse fluorine-containing unities. However, the cross-coupling of benzyl group with α-trifluoromethyl alkenes has yet to be developed. In this report, we describe a general method for the cross-coupling of benzylzinc reagents with 2-bromo-3,3,3-trifluoropropene (BTP) to afford diverse α-trifluoromethylalkene derivatives by using Pd(TFA)₂ as catalyst. This method takes advantage of cheap industrial available fluorine building blocks and easily prepared benzylzinc reagents to generate α-trifluoromethylalkene derivatives, which features with mild reaction conditions, wide substrate scope and feasibility of product transformations.

Graphical Abstract

Keywords:

• Trifluoromethylation
• BTP
• benzylzinc reagents
• palladium-catalyzed

Additional information

Funding

The National Natural Science Foundation of China [No. 81760624, 21702241, 21762053], Young Elite Scientists Sponsorship Program by Cast of the China Association for Science and Technology [No. 2015-41], the Programs of Guizhou Province [No. 2017-1225, 2018-1427] are warmly acknowledged for funding this work.