Selective aryl-fluoride reductive elimination from a platinum(IV) complex

Ina Dubinsky-Davidchik; Israel Goldberg; Arkadi Vigalok; Andrei N Vedernikov

doi:10.1002/anie.201503116

Selective aryl-fluoride reductive elimination from a platinum(IV) complex

Angew Chem Int Ed Engl. 2015 Oct 12;54(42):12447-51. doi: 10.1002/anie.201503116. Epub 2015 Jun 19.

Authors

Ina Dubinsky-Davidchik¹, Israel Goldberg¹, Arkadi Vigalok², Andrei N Vedernikov³

Affiliations

¹ School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978 (Israel).
² School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978 (Israel). avigal@post.tau.ac.il.
³ Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA). avederni@umd.edu.

PMID: 26095826
DOI: 10.1002/anie.201503116

Abstract

A difluoro(mesityl)platinum(IV) complex underwent highly selective reductive elimination of 2-fluoromesitylene upon heating in toluene. Kinetic analysis and DFT calculations suggest that the CF coupling involves a five-coordinate Pt(IV) transient intermediate resulting from the rate-limiting dissociation of the pyridine ligand.

Keywords: chemoselectivity; electrophilic fluorination; platinum; reaction mechanisms; reductive elimination.