Issue 1, 2012

C(sp3)–F reductive elimination from alkylgold(iii) fluoride complexes

Abstract

Rare examples of C(sp3)–F reductive elimination were observed from several cis-F2Au(R)(IPr) intermediates generated by oxidation of (IPr)AuR complexes with XeF2. For R groups bearing β-hydrogens, β-hydride elimination was competitive with C(sp3)–F reductive elimination. For strained cyclic R groups and most acyclic R groups lacking β-hydrogens, carbocation-like rearrangements occurred prior to C(sp3)–F reductive elimination. Kinetics of the decay of one cis-F2Au(R)(IPr) species, stereochemical analysis of reductive elimination with a chiral R group, and DFT analysis collectively suggest C(sp3)–F reductive elimination proceeding through transient cationic [(IPr)Au(F)(R)]+ intermediates with significant ionization of the Au–alkyl bonds.

Graphical abstract: C(sp3)–F reductive elimination from alkylgold(iii) fluoride complexes

Supplementary files

Article information

Article type
Edge Article
Submitted
29 Jul 2011
Accepted
30 Sep 2011
First published
13 Oct 2011

Chem. Sci., 2012,3, 72-76

C(sp3)–F reductive elimination from alkylgold(III) fluoride complexes

N. P. Mankad and F. D. Toste, Chem. Sci., 2012, 3, 72 DOI: 10.1039/C1SC00515D

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