Synergistic Photoredox and Iron(II) Catalyzed Carbophosphorothiolation of Vinyl Arenes

Abstract

A three-component vicinal carbophosphorothiolation of vinyl arenes by the cooperation of visible light and iron(II) catalysis has been established for the synthesis of S-alkyl phosphorothioates. Noteworthy, the late-stage functionalization of biologically active compounds has been performed using this procedure. The preliminary mechanistic study reveals that the catalytic cycle is accomplished by single-electron transfer (SET).

Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

“…Our group realized photoredox/copper-catalyzed fluoroalkylphosphorothiolation and sulfonylphosphorothiolation of alkenes, which underwent the radical addition to alkene and then C­(sp 3 )-phosphorothiolation (Scheme a) . Later, a photoredox/iron-catalyzed carbophosphorothiolation of alkenes has also been reported by the Hajra group . Meanwhile, 2-pyrrolidinone skeletons could be facilely constructed from N -allylbromoacetamides via intramolecular cyclization, and functionalized 2-pyrrolidone derivatives were successfully prepared by several groups through a radical tandem cyclization/coupling process .…”

Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update

“…In spite of these extensive reports, there is no review exist for electrochemical and/or photochemical synthesis of oxazoles and isoxazoles. In continuation to our efforts on photochemical [27][28][29][51][52][53][54][55][56] and electrochemical [45][46][57][58] synthesis and functionalization of heterocycles, we wish to report herein a comprehensive review on photochemical and electrochemical synthesis of oxazole and isoxazoles. In this review, we have highlighted all the recent references on photochemical and electrochemical synthesis of oxazoles as well as isoxazoles.…”

Hydro-phosphorothiolation of Styrene and Cyclopropane with S-Hydrogen Phosphorothioates under Ambient Conditions

“…14 Despite the progress in this area, hydro-phosphorothiolation of alkene remains unexplored. In light of our tireless efforts to functionalize alkene, 15 herein we present a practical and operationally simple method for the hydro-phosphorothiotion of styrenes and D−A cyclopropanes to access S-alkyl phosphorothioates via direct C−S bond formation (Scheme 1d).…”