Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals

Abstract

A novel strategy was developed to generate silyl radicals from silylboronic pinacol esters (SPEs) through nucleohomolytic substitution of boron with aminyl radicals. We successfully applied this strategy to obtain diverse organosilicon compounds using SPEs and N-nitrosamines under photoirradiation without any catalyst. The ability to access silyl radicals offers a new perspective for chemists to rapidly construct Si−X bonds.

Photoredox-Catalyzed Amino-Radical-Transfer-Mediated Three-Component Alkylarylation of Alkenes

“…Based on the above evidence and previous literature reports, , a plausible mechanism was proposed for this three-component transformation (Scheme ). The exited-state photocatalyst [Ir­(dtbpy)­(ppy) 2 PF 6 ]* first reacted with 3 ( E 1/2 ox = −0.93 vs SCE) to produce radical ion F and Ir­(IV).…”