Nickel(0)-catalyzed fluoroalkylation of alkenes, alkynes, and aromatics with perfluoroalkyl chlorides

X T Huang; Q Y Chen

doi:10.1021/jo010178j

Nickel(0)-catalyzed fluoroalkylation of alkenes, alkynes, and aromatics with perfluoroalkyl chlorides

J Org Chem. 2001 Jun 29;66(13):4651-6. doi: 10.1021/jo010178j.

Authors

X T Huang¹, Q Y Chen

Affiliation

¹ Laboratory of Fluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, 200032, Shanghai, China.

PMID: 11421787
DOI: 10.1021/jo010178j

Abstract

Treatment of perfluoroalkyl chlorides (R(F)Cl) with alkenes, alkynes, or aromatics in the presence of 0.1 equiv of nickel dichloride, 1.5 equiv of zinc powder, and 0.4 equiv of triphenylphosphine in DMF at 95-100 degrees C for 6-8 h give the corresponding perfluoroalkylated products in good yields. A single electron-transfer mechanism is suggested.

Publication types

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

MeSH terms

Alkenes / chemistry*
Alkynes / chemistry*
Catalysis
Fluorocarbons / chemistry*
Hydrocarbons, Aromatic / chemistry*

Substances

Alkenes
Alkynes
Fluorocarbons
Hydrocarbons, Aromatic