Addition of ArSSAr to carbon–carbon multiple bonds using electrochemistry

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

“…The reactions were examined at −78 °C, −50 °C, −20 °C, and 0 °C (Table 1, entries 1–4), and the reaction at −50 °C gave the best results (Table 1, entry 2) 10. The addition took place anti‐selectively, which was confirmed by comparison of the NMR spectra of the products with those reported in the literature,3a except the case of the reaction at 0 °C (Table 1,entry 4).…”

“…0.06 mmol), which was generated and accumulated by the electrolysis of ArSSAr (1.0 mmol) by using 0.06 F mol −1 electricity, to give the corresponding diarylthiolated product 14 in 87 % yield (Scheme ). The reaction was highly stereoselective, and the stereochemistry of the product was identified as E by the comparison of the NMR spectra with those reported in the literature 3a…”

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

“…505–510 The thiirane could be opened directly with hard nucleophiles such as fluorides or alkoxides. Nevertheless, due to the presence of disulfides in solution, treatment of the episulfonium with soft nucleophiles led to the formation of vicinal disulfides instead.…”

Recent Developments in the ^|^ldquo;Cation Pool^|^rdquo; Method

“…41 In addition, reactions of ArS(ArSSAr) with alkenes and alkynes give the corresponding diarylthiolated compounds. 42 At higher temperatures such as 0 thio uorination of alkenes and alkynes takes place. Here the counteranion, BF 4 acts as a uoride donor.…”