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

preprint
submitted on 31.03.2021, 21:14 and posted on 01.04.2021, 13:04 by Sumin Lee, Tomislav Rovis

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 a-amino acid derivatives in good yield and excellent 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 3-component coupling products in preference to a variety of 2-component undesired by-products.

Funding

GM80442

History

Email Address of Submitting Author

tr2504@columbia.edu

Institution

Columbia University

Country

United States

ORCID For Submitting Author

0000-0001-6287-8669

Declaration of Conflict of Interest

none

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