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Oxidative Addition, Transmetalation, and Reductive Elimination at a 2,2′-Bipyridyl-Ligated Gold Center

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)4440-4445
Number of pages6
JournalJournal of the American Chemical Society
Volume140
Issue number12
Early online date19 Mar 2018
DOIs
DateAccepted/In press - 5 Feb 2018
DateE-pub ahead of print - 19 Mar 2018
DatePublished (current) - 28 Mar 2018

Abstract

Three-coordinate bipyridyl complexes of gold, [(κ2-bipy)Au(η2-C2H4)][NTf2], are readily accessed by direct reaction of 2,2′-bipyridine (bipy), or its derivatives, with the homoleptic gold ethylene complex [Au(C2H4)3][NTf2]. The cheap and readily available bipyridyl ligands facilitate oxidative addition of aryl iodides to the Au(I) center to give [(κ2-bipy)Au(Ar)I][NTf2], which undergo first aryl-zinc transmetalation and second C-C reductive elimination to produce biaryl products. The products of each distinct step have been characterized. Computational techniques are used to probe the mechanism of the oxidative addition step, offering insight into both the origin of the reversibility of this process and the observation that electron-rich aryl iodides add faster than electron-poor substrates. Thus, for the first time, all steps that are characteristic of a conventional intermolecular Pd(0)-catalyzed biaryl synthesis are demonstrated from a common monometallic Au complex and in the absence of directing groups.

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    Rights statement: This is the final published version of the article (version of record). It first appeared online via ACS Publications at https://doi.org/10.1021/jacs.8b01411 . Please refer to any applicable terms of use of the publisher.

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