Synthesis of fluoroolefin derivatives by nickel(II)-catalyzed trifluorovinylation and 1,2,2-trifluoroethylation of cinnamyl alcohols

Haifeng Wu; Min Zhou; Li Qiao; Pengfei Zhang

doi:10.1039/d2ob01078j

Synthesis of fluoroolefin derivatives by nickel(II)-catalyzed trifluorovinylation and 1,2,2-trifluoroethylation of cinnamyl alcohols

Org Biomol Chem. 2022 Aug 24;20(33):6537-6541. doi: 10.1039/d2ob01078j.

Authors

Haifeng Wu^{1

2}, Min Zhou², Li Qiao², Pengfei Zhang^{1

2}

Affiliations

¹ College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China.
² College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, China.

PMID: 35900033
DOI: 10.1039/d2ob01078j

Abstract

Nickel(II)-catalyzed regioselective trifluorovinylation and 1,2,2-trifluoroethylation of allyl alcohols with trifluorovinyl reagents were performed. The reaction of (E)-3-phenylprop-2-en-1-ol and trifluorovinylzinc bromide (TFVZ) afforded 1,2,2-trifluorovinyl diene in moderate to high yields. The reaction of (E)-3-phenylprop-2-en-1-ol and trifluorovinyl trimethylsilane (TFVTMS) resulted in the novel nucleophilic addition product 1,1,2-trifluoroethoxy aryl olefin.

Publication types

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

MeSH terms

Alkenes*
Catalysis
Indicators and Reagents
Nickel*
Propanols

Substances

Alkenes
Indicators and Reagents
Propanols
Nickel
cinnamyl alcohol