Switchable Synthesis of Sulfoxides and α-Alkoxy-β-ketothioethers Regulated by Temperature in a Selectfluor–Methanol System

Abstract

A switchable and benign protocol for chemoselective synthesis of sulfoxides and α-alkoxy-β-ketothioethers has been developed. It was determined that various thiophenols and alkenes/alkynes are compatible to realize the target compounds from a medium to a high yield by regulating the reaction temperature. In particular, methanol not only served as a solvent but also participated in the reaction process as a hydrogen donor. In this study, Selectfluor has been proved to be an efficient multifunctional reagent in the reaction system.

Additive-Free Construction of Tetrahydropyrimidine Skeleton by using 1,3,5-Triazinane as Four-Atom Synthon

“…As expected, variations in the reaction temperature had a noticeable impact on the reaction (entries 10–12). The production of byproduct 4a was suppressed at temperatures below 90 °C . Furthermore, tetrahydropyrimidine 3a could be isolated with an 85% yield at 90 °C in NMP without an additional additive (entry 11).…”

Visible Light-Promoted Synthesis of β-Keto Sulfoximines from N-Tosyl-Protected Sulfoximidoyl Chlorides

“…Next, A adds to aryl alkyne 2 providing vinyl radical B , which reacts with dioxygen to give peroxy radical C . As suggested in analogous processes, complex , radicals like C can convert to alkoxy radicals E , probably via “dimeric” intermediates D , which undergo homolytic cleavage of the central O–O bond. If E abstracts a hydrogen from THF, , enol F is formed, which tautomerizes to give product 3 .…”