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Updated: Jul 3, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Acid-catalyzed C-H reductive elimination from Au(iii)
Yotam Ardon1, Michael R Gau1, Karen I Goldberg1
1Department of Chemistry, University of Pennsylvania 231 S 34th St Philadelphia PA 19104 USA kig@sas.upenn.edu.
Abstract:
An unusual mode of C-H reductive elimination from a AuIII complex catalyzed by acid is reported. The addition of triflic acid (HOTf) to [( tBuPCP)AuIII-H]OTf (1-OTf, tBuPCP = 2,6-C6H3(CH2P t Bu2)2 promotes formal C-H reductive elimination. The AuI product [( tBuP(C-H)P)AuI]OTf (2-OTf, tBuP(C-H)P = κ2(1,3-C6H4(CH2P t Bu2)2)) was characterized by NMR spectroscopy and X-ray diffraction. It was shown that the reductive elimination of 1-OTf has a dependence on the identity of the acid catalyst which cannot be explained by acid strength. Mechanistic experiments are consistent with a concerted mechanism for C-H reductive elimination involving participation of basic moieties on the acid.
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