title: Gold-Catalyzed Proto- and Deuterodeboronation.
abstract: 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.
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Graeme
authors.initials: G
authors.lastname: Barker
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Stacey
authors.initials: S
authors.lastname: Webster
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: David G
authors.initials: DG
authors.lastname: Johnson
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Rachel
authors.initials: R
authors.lastname: Curley
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Matthew
authors.initials: M
authors.lastname: Andrews
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Paul C
authors.initials: PC
authors.lastname: Young
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Stuart A
authors.initials: SA
authors.lastname: Macgregor
authors.affiliation: Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS United Kingdom.
authors.forename: Ai-Lan
authors.initials: AL
authors.lastname: Lee