Reusable and efficient CoCl2·6H2O/cationic 2,2’-bipyridyl system-catalyzed S-arylation of aryl halides with thiols in water under air

Abstract

A CoCl 2 ?6H 2 O/cationic 2,2'-bipyridyl system was proven to be an efficient and reusable catalyst for the coupling of aryl halides with thiols in water under aerobic conditions, leading to the formation of thioethers. Aryl iodides and bromides could couple with various thiols giving the corresponding thioethers using only a 3 mol% catalyst loading in the presence of 1 equiv KOH and 1.5 equiv Zn at 100 uC. For aryl chlorides, reaction at 140 uC and prolongation of the reaction time was performed. After reaction, the residual aqueous solution could be reused several times without any additional treatment and regeneration, making this cobalt-catalyzed S-arylation reaction greener.

Transition‐Metal‐Catalyzed CS Bond Coupling Reaction

“…Whereas aryl iodides and bromides could be used for the coupling with alkyl thiols, aryl chlorides were found to be totally inert in this reaction. [83] Representative examples are given.…”

Recent Achievements in Organic Trithiocarbonates Synthesis

“…47 During the last decades, the use of metal catalysts to form C−S bonds played an important and valuable role in organosulfur chemistry. 48 Copper catalysts are the most common metal catalysts for the synthesis of compounds with C−S bonds. 49,50 In this respect, Gholinejad used copper(I) iodide to prepare symmetrical diaryl trithiocarbonates via onepot reactions of aryl halides, sodium sulfide, and carbon disulfide in dimethylformamide (Scheme 18).…”

An Efficient Heterogeneous Cu-Grafted Mesoporous Organosilicas Nanocatalyst for Two and Three Component C—S Coupling Reactions

“…36 37 A large variety of aryl sulfides can be employed as drugs for the treatment of diabetes, inflammation, Alzheimer's and Parkinson's disease, 38 cancer 39 and HIV disease. 34 In this context, transition metal catalyzed C S cross coupling [40][41][42][43] reactions have been studied to a less extent compared to C C, C N and C O cross coupling reactions. Favorable S S oxidative coupling reaction resulting in the undesired formation of disulfides and simultaneous deactivation of metal catalyst as organic sulfur compounds are effective metal binders, make the C S cross coupling reaction quite inauspicious.…”

“…Favorable S S oxidative coupling reaction resulting in the undesired formation of disulfides and simultaneous deactivation of metal catalyst as organic sulfur compounds are effective metal binders, make the C S cross coupling reaction quite inauspicious. C S cross-coupling has been performed with the use of several transition metal catalysts such as palladium, 44 45 nickel, 46 copper, 41 cobalt, 42 iron, 47 and indium 48 etc. The catalytic system associated with the palladium catalysts for performing C S cross coupling reaction has been employed to a limited extent due to the high cost, air sensitivity of palladium salts and the use of environmentally harmful organophosphorous ligands.…”