9 Gold in Photocatalysis

Abstract

Dual catalytic systems combining gold and photocatalysis are capable of facilitating redox-neutral coupling reactions that are otherwise seldom observed using gold catalysts alone. The challenging oxidation of gold(I) to gold(III) in these processes is achieved through two single-electron-transfer steps involving photogenerated organic radicals derived most commonly from arenediazonium salts. In addition to analogues of some classical cross-coupling processes that are tolerant of halogen functionalities, arylative 1,2-difunctionalization reactions of π-systems, combining the traditional π-Lewis acidity of gold catalysts with coupling, are accessible. These processes can be performed on alkene, allene, and alkyne substrates with the unique mechanistic features of dual gold/photoredox catalysis allowing for improved selectivity for cross coupling compared to that observed in alternative oxidative gold-catalyzed coupling methodologies.

Key words

photocatalysis - gold catalysis - photoredox catalysis - cross coupling - 1,2-difunctionalization - arylation - diazonium salts - dual catalysis - visible light - alkenes - allenes - alkynes - redox-neutral coupling - radical intermediates - aryl radicals

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