Gold-Catalyzed Proto- and Deuterodeboronation

Graeme Barker, Stacey Webster, David G. Johnson, Rachel Curley, Matthew Andrews, Paul C. Young, Stuart A. MacGregor*, Ai Lan Lee

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.

Original languageEnglish
Pages (from-to)9807-9816
Number of pages10
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 16 Oct 2015


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