Photoinduced remote C-N/C bond formation via ring-opening 1,4-difunctionalization of methylenecyclobutanes.

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.