Rhodium(III)-catalyzed chelation-assisted ortho-selective carbon−hydrogen alkylation of phenols with diazocarbonyl compounds involving a carbene migratory insertion process

Abstract

An efficient and convenient rhodium(III)-catalyzed chelation-assisted ortho-selective carbon−hydrogen bond alkylation of phenols treated with readily available diazocarbonyl compounds as the alkyl source has been described. Migratory carbene insertion represents the principal step to realize this carbenoid coupling transformation, giving rise to a broad rang of alkylated products and at the same time, releasing nitrogen gas as sole byproduct. This protocol offers exclusive regioselectivities, moderate to excellent chemical yields, and good functional group tolerance.

Keywords

• Rhodium catalysis
• Phenol
• Diazocarbonyl compound
• C−H bond functionalization
• Alkylation
• Carbene insertion