60372-32-9

Upstream product

• 108-85-0 1-bromocyclohexane 
• 615-22-5 2-methylmercaptobenzothiazole 
• 98-89-5 Cyclohexanecarboxylic acid 
• 149-30-4 2-Mercaptobenzothiazole 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 110-82-7 cyclohexane 
• 103-19-5 di(p-tolyl) disulfide 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 95-16-9 1,3-Benzothiazole 
• 1569-69-3 Cyclohexanethiol 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 2492-26-4 sodium 2-mercaptobenzothiazole 

Downstream Products

• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 110-83-8 cyclohexene 
• 202002-02-6 3-cyclohexylbenzo[d]thiazole-2(3H)-thione 
• 95091-06-8 2-cyclohexanesulfonyl-benzothiazole 
• 95-16-9 1,3-Benzothiazole 
• 34009-02-4 ((cyclohexylsulfonyl)methyl)benzene 
• 74829-95-1 sodium cyclohexane sulfinate 

Relevant academic research and scientific papers

Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.

Metal-free preparation of cycloalkyl aryl sulfides via di-tert-butyl peroxide-promoted oxidative C(sp3)-H bond thiolation of cycloalkanes

A concise thiolation of the C(sp3)-H bond of cycloalkanes with diaryl disulfides in the presence of the oxidant di-tert-butyl peroxide (DTBP) has been developed. This reaction, without using any metal catalyst, tolerates varieties of disulfides and cycloalkanes substrates, giving good to excellent chemical yields, and thus provides a useful approach to cycloalkyl aryl sulfides from unactivated cycloalkanes.

Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond

A new protocol for C-S and C-Se bond formation by the direct functionalization of the C(sp3)-H bond of alkanes under metal-free conditions was developed. Using tBuOOtBu as the oxidant, the reaction of disulfides or diselenides with alkanes gave sulfides or selenides in moderate to good yields. The method was very simple and atom-economical.

N-heterocyclic carbene copper(I) complex-catalyzed direct C-H thiolation of benzothiazoles

N-heterocyclic carbene (NHC) copper(I) complexes based on imidazol-2-ylidene and 1,2,3-triazol-5-ylidene catalyzed the direct C-H thiolation of benzothiazoles and benzoxazoles with aryl and alkyl thiols to give 2-aryl and 2-alkylthiobenzothiazoles in moderate-to-good yields. The NHC copper(I) complex [(IPr)CuI] was the most effective catalyst for the reaction among the NHC-Cu(I) complexes examined in this study.

Lewis acid-catalyzed, copper(II)-mediated synthesis of heteroaryl thioethers under base-free conditions

A Lewis acid (AgI, NiII, or FeII) catalyzed, CuII-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic methyl thioethers.

Copper-mediated C-H activation/C-S cross-coupling of heterocycles with thiols

We report the synthesis of a series of aryl- or alkyl-substituted 2-mercaptobenzothiazoles by direct thiolation of benzothiazoles with aryl or alkyl thiols via copper-mediated aerobic C-H bond activation in the presence of stoichiometric CuI, 2,2′-bipyridine and Na2CO3. We also show that the approach can be extended to thiazole, benzimidazole, and indole substrates. In addition, we present detailed mechanistic investigations on the Cu(I)-mediated direct thiolation reactions. Both computational studies and experimental results reveal that the copper-thiolate complex [(L)Cu(SR)] (L: nitrogen-based bidentate ligand such as 2,2′-bipyridine; R: aryl or alkyl group) is the first reactive intermediate responsible for the observed organic transformation. Furthermore, our computational studies suggest a stepwise reaction mechanism based on a hydrogen atom abstraction pathway, which is more energetically feasible than many other possible pathways including β-hydride elimination, single electron transfer, hydrogen atom transfer, oxidative addition/reductive elimination, and σ-bond metathesis.