Atom Transfer Oxidative Radical Cascade of Aryl Alkynoates towards 1,1‐Dichalcogenide Olefins

Abstract

on the occasion of his 80th birthday Scheme1.Radical-based cascade rearrangement of aryl alkynoates towards functionalized alkenes.Scheme3.Substrate scope for twofold smiles rearrangement of aryl alkynoates.Scheme4.Post-functionalizations.Scheme5.Control experiments.Scheme6.Plausible reaction mechanism.

Recent Developments in the Synthesis of Organoselenium Compounds Based on the Reactions of Organic Diselenides with Acetylenes

“…This methodology can be used in the synthesis of vinyl selenides and 1,1-dichalcogenyl olefins [107,108].…”

“…This radical-based cascade reaction was carried out at room temperature in the presence of tert-butyl hydroperoxide (TBHP) and studied with the use of devices. This methodology can be used in the synthesis of vinyl selenides and 1,1-dichalcogenyl olefins [107,108].…”

Recent Advances in the Tandem Difunctionalization of Alkynes: Mechanism-Based Classification

“…In 2019, they also reported the radical cascade of aryl alkynoates towards 1,1-dichalcogenide alkenes. 37 Decarboxylation gave a vinyl radical species, which subsequently underwent coupling with a diaryl diselenide (or aryl selenium radical) (Scheme 28).…”

Mechanistic insight for tunable regioselective cyclization of aryl propiolates with radicals:ipso-versus ortho-cyclization

“…34 In addition to coumarin derivatives, styrene derivatives can also be formed depending on the reaction temperature. 35–39 All plausible mechanisms for the reaction of aryl propiolates 1 with various radicals are given in Scheme 1. According to the mechanism, an electrophilic attack of radical 2 at the α-position of the triple bond yields radical 3 .…”

“…34 In addition to coumarin derivatives, styrene derivatives can also be formed depending on the reaction temperature. [35][36][37][38][39] All plausible mechanisms for the reaction of aryl propiolates 1 with various radicals are given in Scheme 1.…”