Electrochemical phosphorothiolation and 1,4-S → C phospho-Fries rearrangement: controlled access to phosphorothiolated and mercapto-phosphono substituted indolizines

Abstract

An unprecedented electrochemically regioselective C–H phosphorothiolation and S- to C-[1,4] phosphonyl migration involving indolizines, elemental sulfur, and H-phosphonates in an undivided cell has been developed.

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds

“…Almost concurrently, Cao and coworkers disclosed a single example of electrochemical C–H bis-phosphorothiolation by treatment of 2-(3,4-dichlorophenyl)indolizine 91b with elemental sulfur and diethyl phosphonate 99 in an undivided cell using Et 3 N as the base and KBr as both a mediator and a supporting electrolyte (Scheme 33). 171 Furthermore, an electrochemical C–H phosphorodithiolation of 2-arylindolizines 91 was also realized by using (MeO) 2 P(S)SH 100 as the coupling partner.…”

TsCl promoted deoxygenative phosphorothiolation of quinoline N-oxides towards S-quinolyl phosphorothioates

“…16 Most recently, Cao and co-workers developed an electrochemical phosphorothiolation of indolizines with elemental sulfur and P(O)H compounds (Scheme 1c). 17 Despite these delightful advances, the development of more efficient and practical strategies for the preparation of other heterocyclic phosphorothioates is still in urgent demand and remains a great challenge.…”