Approach to Access Benzo[j]phenanthridinones from 1,7-Enynes and Aryldiazonium Salts via a Domino Radical Relay Process Enabled by a P/N-Heteroleptic Cu(I)-Photosensitizer.

Abstract

A mild approach for the synthesis of benzo[j]phenanthridin-6(5H)-one derivatives from 1,7-enynes and aryldiazonium salts has been successfully developed involving a domino radical relay process enabled by a heteroleptic Cu(I)-photosensitizer under visible-light-driven photocatalytic conditions. Mechanistic studies disclosed that the oxidative quenching of the excited state of PS 4 with aryldiazonium salts via an SET process generated aryl radicals, which could play a radical initiator-terminator dual role within the whole radical relay process, namely, at the initial step acting as a radical donor to trigger the radical addition to the olefin moieties of 1,7-enynes while at the final stage serving as a radical acceptor to complete the cyclization.