Photoinduced remote C–N/C bond formationring-opening 1,4-difunctionalization of methylenecyclobutanes

Source: PubMed Central Open Access, NCBI / U.S. National Library of Medicine

The construction of C–N bonds is a fundamental transformation in organic synthesis. While significant progress has been made in C–N bond formation at the alkene π-bond or at the allylic position, achieving remote C–N bond formation remains a considerable challenge. Herein, we report a photochemical strategy for remote 1,4-difunctionalization to forge C–N bonds, enabled by strain-induced ring-opening of methylenecyclobutanes. Using pyrazole or acetonitrile as nitrogen nucleophiles, this method delivers a range of bishomoallylic amine derivatives. Notably, the protocol is also extendable to C–C bond formation with carbon nucleophiles, including pyrroles, indoles, naphthol, and electron-rich arenes. We report a photochemical strategy for remote 1,4-difunctionalization to forge C–N and C–C bonds, enabled by strain-induced ring-opening of methylenecyclobutanes. toc