Au-Catalyzed Oxidative Arylation: Chelation-Induced Turnover of ortho-Substituted Arylsilanes

Matthew P. Robinson, Guy C. Lloyd-jones

Research output: Contribution to journalArticlepeer-review

Abstract

Ortho-substituted aryl silanes have previously been found to undergo much slower Au-catalyzed intermolecular arylation than their m,p-substituted isomers, with many examples failing to undergo turnover at all. A method to indirectly quantify the rates of C–Si auration of o-substituted aryl silanes, under conditions of turnover, has been developed. All examples are found to undergo very efficient C–Si auration, indicative that it is the subsequent C–H auration that is inhibited by the ortho substituent. A simple Ar-Au conformational model suggests that C–H auration can be accelerated by chelation. A series of ortho-functionalized aryl silanes are shown to undergo efficient arylation.
Original languageEnglish
Pages (from-to)7484-7488
JournalACS Catalysis
Volume8
Issue number8
Early online date17 Jul 2018
DOIs
Publication statusPublished - 3 Aug 2018

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