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

Abstract

Migration of a remote aryl group is a state-of-the-art strategy for difunctionalization of alkenes strategy. Herein, we report a method for visible-light-induced sulfonylarylation reactions of unactivated alkenes via 1,4-(hetero)aryl migration...

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate

“…Based on the above experiments and reference-related literature (Figure ), , we proposed a feasible reaction mechanism in Figure . Eosin Y changes from a ground state to an excited state after Eosin Y absorbs light energy.…”

“…We have previously reported visible light-triggered heteroaryl migration/desulfonylation reaction by using teteroarylalkenes and thiosulfonate . Afterward, Wang et al and Wang et al reported similar reactions. These strategies − are good to achieve the dual function of unactivated olefins.…”

Photoredox Metal‐Free Synthesis of Unnatural β‐Silyl‐α‐Amino Acids via Hydrosilylation

“…The authors have cited additional references within the Supporting Information. [24][25][26][27][28]…”

Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis

“…Organic photoredox catalysis is a green, mild, and highly efficient synthetic tool, which has been applied to the construction of carbon–carbon and carbon–heteroatom bonds . Even though some alkenes can undergo cascade distal arylation migration with radicals via organic photocatalysis, such as trifluoro radicals, sulfonyl/sulfinyl radicals, fluorine-containing radicals, arylphosphonyl/acyl radicals, etc., little attention has been paid to organic photoredox silyl-mediated aryl/alkenyl migration of unactivated alkenes. With our continuous efforts in photomediated construction of carbon–silicon bonds by the addition of silyl radicals to unsaturated chemical bonds with hydrosilanes, we envisioned that, under the right set of conditions, silyl-mediated (hetero)­aryl/alkenyl migration reactions could be processed after the addition of silyl radicals to unactivated alkenes bearing (hetero)­aryl/alkenyl amines, enabling the simultaneous incorporation of silyl and (hetero)­aryl/alkenyl groups to alkenes, which would be beyond the well-established synthesis of organosilicon compounds.…”