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Issue 1, 2012
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C(sp3)–F reductive elimination from alkylgold(III) fluoride complexes

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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

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The article was received on 29 Jul 2011, accepted on 30 Sep 2011 and first published on 13 Oct 2011

Article type: Edge Article
DOI: 10.1039/C1SC00515D
Chem. Sci., 2012,3, 72-76

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    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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