Addition of ArSSAr to dienes via intramolecular C–C bond formation initiated by a catalytic amount of ArS+

Abstract

A catalytic amount of electrochemically generated "ArS+" ("ArS+" = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon-carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction.

Alternating Current Electrolysis for the Electrocatalytic Synthesis of Mixed Disulfide via Sulfur–Sulfur Bond Metathesis towards Dynamic Disulfide Libraries

“…[12] Latter speciesa re believed to undergo as eries of RS + -transfer reactions in organicc hemistry. [13] On the other hand, under reductive conditions, radical anionsc an be generated which dissociate to form thiyl radicals (R-SC)a nd at hiolate anion. [14] Also, two electron-transfer process are described so that the disulfides are converted to the corresponding thiyl radicals R-SC,c ations RS + or anions RS À .A ccordingly,u nder both electrochemical conditions, reactive species are formed which undergo various reactions with other startingm aterials.…”

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…515,516 Furthermore, the “ArS + cation pool” was utilized (in catalytic amounts) to initiate olefin cyclization reactions, forming both heterocyclic and carbocyclic rings (Figure 33C). 517,518 …”

The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+

“…We envisioned that the addition reaction of ArSSAr to alkenes may proceed with a catalytic amount of ArS(ArSSAr) + if another molecule of ArSSAr plays the role of a soft nucleophile. This is indeed the case if we use Bu 4 NB(C 6 F 5 ) 4 as a supporting electrolyte, and herein, we report the details of this chemistry (Scheme ) 9…”

“…The present reaction seems to proceed by the cation chain mechanism3i, 9, 11 shown in Scheme . A catalytic amount of 1 reacts with an alkene to give thiiranium ion intermediate A .…”