Regioselective Radical Cascade Cyclizations of Alkyne-Tethered Cyclohexadienones with Chalcogenides under Visible-Light Catalysis.

Herein, we demonstrated a silver/K2S2O8-mediated highly regio- and diastereoselective 6/5-exo trig radical cascade cyclization of alkyne-tethered cyclohexadienones with sulfonyl hydrazides or sodium sulfinates and subsequent selenation to access 6,6-dihydrochromenone and 6,5-fused tetrahydro benzofuranone derivatives. This reaction protocol features high functional group compatibility and has a wide substrate scope providing a variety of dihydrochromenones and tetrahydro benzofuranone derivatives in good to excellent yields. The reaction proceeds via the attack of a sulfonyl radical to alkyne over the activated Michael acceptor. The TEMPO quenching experiment implies the presence of a radical intermediate. Further synthetic versatility of 6,6- and 5,6-fused derivatives is also showcased.