Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides

Abstract

The site-selective C-H functionalization of arenes is of indisputable importance in organic chemistry. Herein, we demonstrated an electrochemical regioselective oxidative cross-coupling towards the direct C(sp2)-H sulfinylation of phenols with sulfides...

Electrochemical 1,3‐Oxofluorination of Gem‐Difluoro Cyclopropanes: Approach to α‐CF3‐Substituted Carbonyl Compounds

“…In the last decade, electro‐organic synthesis has emerged as a useful method for performing advantageous organic transformations [17] to achieve specific oxidative or reductive reactions such as decarboxylation, [18a] alkene bifunctionalization, [18b] rearrangements, [18c] annulations, [18d] and C−C or C‐heteroatom bond formation [18e–i] . In 2021, Lei et al .…”

Recent Advances in Regioselective C–H Bond Functionalization of Free Phenols

“…A variety of substrates, including C2-substituted benzothiophene S-oxides and C3-substituted benzothiophene S-oxides, were successfully used in the arylated reaction to realize the C-H bond functionalization of free phenols. However, when using 4- Recently, the Banerjee group [59] further developed an electrochemical sulfinylation of free phenols 162 with sulfides 163 under catalyst-and oxidant-free conditions. The aromatic sulfoxides 164 were obtained with 38-65% yields in an undivided cell equipped with a graphite anode and a nickel cathode at a constant current of 15 mA, using n-Bu 4 NPF 6 as the electrolyte at room temperature (Scheme 27).…”

“…Control experiments suggested that the electrochemical sulfonated reaction was proposed to initiate via the anodic oxidation of phenol to generate carbocation, which was then attacked by the nucleophilic sulfide to generate the desired product. Recently, the Banerjee group [59] further developed an electrochemical sulfinylation of free phenols 162 with sulfides 163 under catalyst-and oxidant-free conditions. The aromatic sulfoxides 164 were obtained with 38-65% yields in an undivided cell equipped with a graphite anode and a nickel cathode at a constant current of 15 mA, using n-Bu4NPF6 as the electrolyte at room temperature (Scheme 27).…”

Electro-oxidative coupling of Bunte salts with aryldiazonium tetrafluoroborates: a benign access to unsymmetrical sulfoxides

“…The most prevalent approach to achieve sulfoxides involves the oxidation of organic sulfides using peroxides, 11 a,b oxone, 11 c IBX/Et 4 NBr, 11 d aerobic photocatalysis, 11 e,f and electrochemical techniques. 12 Some recent and relevant reports for the synthesis of sulfoxides are shown in Scheme 1. Jiang et al have developed an efficient sulfoxidation reaction using thiosulfates and diaryl iodonium salts in the presence of eosin Y, DIPEA, and Zn(OAc) 2 under green LED irradiation (Scheme 1A).…”