Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones

Herein, we report a Rh(III)-catalyzed three-component carboamination of alkenes from readily available aryl boronic acids as a carbon source and dioxazolones as nitrogen electrophiles. This protocol provides facile access to valuable amine products including alpha-amino acid derivatives in good yield and regioselectivity without the need for a directing functionality. A series of experiments suggest a mechanism in which the Rh(III) catalyst undergoes transmetalation with the aryl boronic acid, followed by turnover limiting alkene migratory insertion into the Rh(III)-aryl bond. Subsequently, fast Rh-nitrene formation provides the syn-carboamination product selectively after reductive elimination and proto-demetalation. Importantly, the protocol provides three-component coupling products in preference to a variety of two-component undesired byproducts.

Automated summary

This study presents a Rh(III)-catalyzed three-component carboamination of alkenes, allowing for the efficient and regioselective synthesis of valuable amine products, including alpha-amino acid derivatives, without the need for directing functionalities.