Dual gold photoredox C(sp2)–C(sp2) cross couplings – development and mechanistic studies

Vincent Gauchot; Ai-Lan Lee

doi:10.1039/C6CC05078F

Dual gold photoredox C(sp2)–C(sp2) cross couplings – development and mechanistic studies

Vincent Gauchot, Ai-Lan Lee

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Abstract

A dual visible light photoredox and gold-catalysed C(sp2)–C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(I) occurs prior to oxidation of gold(I) to gold(III) using cationic gold(I) catalysts, whereas oxidation of gold(I) to gold(III) precedes transmetallation using neutral gold(I) catalysts.

Original language	English
Pages (from-to)	10163-10166
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	66
Early online date	19 Jul 2016
DOIs	https://doi.org/10.1039/C6CC05078F
Publication status	Published - 25 Aug 2016

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title = "Dual gold photoredox C(sp2)–C(sp2) cross couplings – development and mechanistic studies",

abstract = "A dual visible light photoredox and gold-catalysed C(sp2)–C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(I) occurs prior to oxidation of gold(I) to gold(III) using cationic gold(I) catalysts, whereas oxidation of gold(I) to gold(III) precedes transmetallation using neutral gold(I) catalysts.",

author = "Vincent Gauchot and Ai-Lan Lee",

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AU - Lee, Ai-Lan

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N2 - A dual visible light photoredox and gold-catalysed C(sp2)–C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(I) occurs prior to oxidation of gold(I) to gold(III) using cationic gold(I) catalysts, whereas oxidation of gold(I) to gold(III) precedes transmetallation using neutral gold(I) catalysts.

AB - A dual visible light photoredox and gold-catalysed C(sp2)–C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(I) occurs prior to oxidation of gold(I) to gold(III) using cationic gold(I) catalysts, whereas oxidation of gold(I) to gold(III) precedes transmetallation using neutral gold(I) catalysts.

U2 - 10.1039/C6CC05078F

DO - 10.1039/C6CC05078F

M3 - Article

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SP - 10163

EP - 10166

JO - Chemical Communications

JF - Chemical Communications

IS - 66

ER -

Dual gold photoredox C(sp2)–C(sp2) cross couplings – development and mechanistic studies

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