A regioselective copper nitrate‐mediated difunctionalization of alkenes has been developed for the rapid synthesis of β‐bromonitrates, where copper nitrate is used as an ideal nitrooxy source for the first time and the products will find many applications in organic synthesis as versatile synthons. Different from the general reports that copper nitrate acts as the nitro source, the given protocol provides a direct access to functionalized nitrates, with operational simplicity, good functional group tolerance and a wide substrate scope.magnified image

An efficient copper nitrate-mediated difunctionalization of alkenes with N-fluorobenzene-sulfonimide (NFSI) has been developed for the direct synthesis of β-aminonitrates in moderate to excellent yields with high regioselectivity. This reaction proceeds through a radical process, where copper nitrate is used as the nitrate source, NFSI as the nitrogen source. The given protocol provides a direct access to functionalized nitrates with operational simplicity, good functional group tolerance and a wide substrate scope. The reaction can be performed in a gram scale and the synthetic utility of the product is demonstrated.

Comprehensive SummaryAn unprecedented copper nitrate‐mediated bond cleavage of alkynes was developed for the modular synthesis of isoxazoles, where either C–S bond or C≡C triple bond was cleaved selectively. Substituents attached to the C≡C triple bonds could differentiate the chemical bonds cleavage and reaction pathways disparately. Various transformations of products illustrate promising applications of the given protocols.This article is protected by copyright. All rights reserved.