Visible-light-promoted sulfonylation of thiols with aryldiazonium and sodium metabisulphite leading to unsymmetrical thiosulfonates

Abstract

A new visible-light-mediated protocol has been proposed for the synthesis of thiosulfonates via metal-free sulfonylation of thiols with aryldiazonium and sodium metabisulphite at room temperature. This mild three-component reaction, simply...

Metal‐Free Multi‐Component Sulfur Dioxide Insertion Reaction Leading to Quinoxalin‐2‐One‐Containing Vinyl Sulfones under Visible‐Light Photoredox Catalysis

“…On the basis of the above results and related literature, [14,15,18,20–23] we proposed a plausible mechanism of this visible‐light mediated reaction as illustrated in Scheme 3. Initially, photoexcitation of Rhodamine 6G would give rise to the excited state Rhodamine 6G* in the presence of visible‐light irradiation.…”

One-Pot Two-Step Strategy for Efficient Synthesis of 3-Aryl-4-(arylthio)-1H-pyrazol-5-amines Derivatives

“…Subsequently, the ester group is hydrolyzed and removed in the presence of phenylsulfurous acid and NIS to afford the product 3a'. [50] Next, the sulfenylation of 3a is achieved through the following two paths [47b,47c] : Path 1, iodothiobenzene formed by the reaction of 6aa with I 2 undergoes electrophilic substitution with 3a to give interme-…”

The Renaissance of Alkali Metabisulfites as SO2 Surrogates

“…A wide range of substrates worked well with good functional group tolerance (Scheme 59). 78 In 2020, Tang and co-workers described a similar protocol in which simultaneous cleavage of two CC bonds of methylenecyclopropane (71) Recently, N-functionalized pyridinium salts such as Katritzky's salt have been found to be effective alkylating agents under photoredox catalytic process for various transformations. 80 In 2019, Wu and co-workers reported the synthesis of -keto sulfone (74) using Katritzky's salt as an alkyl radical precursor and potassium metabisulfite as the SO2 surrogate (Scheme 63).…”

“…70 A visible-light-promoted synthesis of thiosulfonates 56 was reported by He et al using thiols, aryldiazonium salts 55, and sodium metabisulfite under metal-free conditions (Scheme 46). 71 This mild, three-component reaction utilizes rhodamine 6G as the photocatalyst to provide unsymmetrical thiosulfonates.…”

“…(Scheme 46). 71 This mild three-component reaction utilizes rhodamine 6G as the photocatalyst to provide unsymmetrical thiosulfonates.…”