Nickel(0)-Mediated Transformation of Tetrafluoroethylene and Vinylarenes into Fluorinated Cyclobutyl Compounds

Masato Ohashi; Yuta Ueda; Sensuke Ogoshi

doi:10.1002/anie.201610047

Nickel(0)-Mediated Transformation of Tetrafluoroethylene and Vinylarenes into Fluorinated Cyclobutyl Compounds

Angew Chem Int Ed Engl. 2017 Feb 20;56(9):2435-2439. doi: 10.1002/anie.201610047. Epub 2017 Jan 23.

Authors

Masato Ohashi¹, Yuta Ueda¹, Sensuke Ogoshi¹

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.

PMID: 28111870
DOI: 10.1002/anie.201610047

Abstract

In the presence of Ni⁰ /PCy₃ , styrene was found to participate in oxidative cyclization with tetrafluoroethylene, thus leading to the corresponding nickelacycle with a unique η³ -π-benzyl structure. In addition, the flexibility of the coordination mode in the η³ -benzyl moiety allowed the partially fluorinated nickelacycle to undergo unprecedented amine-induced α-fluorine elimination, thus leading to the construction of a fluorinated cyclobutyl skeleton.

Keywords: amines; fluorine; nickel; reaction mechanisms; synthetic methods.

Publication types

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