Nucleophile Promoted Gold Redox Catalysis with diazonium: CBr, C-S and C-P Bond Formation through Catalytic Sandmeyer Coupling

Abstract

Gold-catalyzed C-heteroatom (C-X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant to convert Au(I) to Au(III) even without the addition of assisting ligand or photocatalyst. By accelerating reaction kinetics to outcompete C-C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C-Br, C-S and C-P bonds in high yields and selectivity

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