Visible-light-induced Smiles rearrangement without release of SO₂: rapid access to alkyl sulfonyl derivatives

Abstract

Conventional visible-light-induced Smiles rearrangements generate C, N, or O radicals and release SO2. Herein, we describe a perfectly atom-economical protocol for Smiles rearrangements without release of SO2. The protocol not...

Visible-light-induced sulfonylarylation of unactivated alkenes via 1,4-(hetero)aryl migration from oxygen or nitrogen to carbon

“…Despite substantial progress in functional group migration reactions for the difunctionalization of unactivated alkenes, the design and development of new, green and economical strategies to accomplish such transformations would be desirable. Inspired by the seminal work described above, the Zhu group reported radical-mediated intermolecular carboarylation of alkenes by cleaving inert C–O bonds, 11 and we recently reported a Smiles rearrangement reaction; 12 we were interested in developing a new method for functionalization of alkenes by radical Smiles–Truce rearrangements not relying on the presence of a sulfonyl group. Herein, we report the results of our investigation of the use of unactivated alkenes bearing distal aryl ether or aromatic amine groups as robust substrates for alkene difunctionalization via a cascade process involving radical addition and remote (hetero)aryl migration.…”