Copper-Catalyzed Selective Three-Component 1,2-Phosphonoazidation of 1,3-Dienes

Org Lett. 2024 Feb 23;26(7):1387-1392. doi: 10.1021/acs.orglett.3c04308. Epub 2024 Feb 11.

Abstract

We report a copper-catalyzed selective 1,2-phosphonoazidation of conjugated dienes. This three-component reaction is achieved by using readily available P(O)-H compounds and bench-stable NaN3. Salient features of this strategy include its mild reaction conditions, broad functional group tolerance, and high chemoselectivity and regioselectivity. Moreover, the compatibility with the late-stage functionalization of drug molecules, the potential for scalable production, and the feasibility of further modifications of the products underscore the practical utility of this protocol in synthetic applications.