62849-63-2

Upstream product

• 933-00-6 p-methylbenzenesulfenyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 106-45-6 para-thiocresol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 103-19-5 di(p-tolyl) disulfide 

Downstream Products

• 51787-23-6 N,N-dimethyl-4-tosylaniline 

Relevant academic research and scientific papers

Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines

A flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the only byproduct.

Two-Step Synthesis of Unsymmetrical Diaryl Sulfides by Electrophilic Thiolation of Non-functionalized (Hetero)arenes

This article reports the efficient preparation of a series of unsymmetrically substituted thioethers through a two-step procedure consisting of an initial metal-free C?H sulfenylation of electron-rich (hetero)arenes with newly prepared succinylthioimidazolium salts. Subsequent reaction of the arylthioimidazolium intermediates with Grignard reagents afford the desired thioethers. The synthetic protocol described is modular, scalable, and high yielding, and provides access to sulfides that are not easy to obtain through the existing methodologies. Importantly, no prefunctionalization of the initial (hetero)arene is required.

Modified conditions for copper-catalyzed ipso-thiolation of arylboronic acid esters with thiosulfonates

An efficient ipso-thiolation of arylboronic acid esters with thiosulfonates has been achieved under mild and odorless conditions using a copper catalyst. The use of TMEDA and cesium fluoride as the ligand and base, respectively, dramatically facilitated the desired transformation. The method exhibited a broad substrate scope, which allowed for the expeditious synthesis of diverse aryl sulfides from easily available starting materials.

Rhodium-catalyzed odorless synthesis of diaryl sulfides from borylarenes and: S -aryl thiosulfonates

Various diaryl sulfides, including heteroaryl- and nitrogen-containing sulfides, have been efficiently prepared by rhodium-catalyzed odorless deborylative arylthiolation of organoborons with S-aryl thiosulfonates. The ready availability of starting materials and further transformation of sulfides have rendered a diverse range of organosulfur compounds easily accessible.

Acid-induced chemoselective arylthiolations of electron-rich arenes in ionic liquids from sodium arylsulfinates: The reducibility of halide anions in [Hmim]Br

An acid-induced protocol for the chemoselective arylthiolations of electron-rich arenes in ionic liquids from sodium arylsulfinates is introduced. The chemistry, in which [Hmim]Br (heaxylmethylimidazolium bromide) is used as both a solvent and a reducer, provides several advantages including odorless and simple operation, inexpensive reagents, recyclable solvents and gram-scale synthesis.

Sodium Iodide (NaI)-Catalyzed Cross-Coupling for C?S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides

A simple and practical NaI-catalyzed direct C?H sulfenylation of arenes has been developed under air. In this reaction, aryl sulfides were obtained in moderate to excellent yields with high regioselectivity from readily available aromatic compounds and aryl/alkyl thiols, even on gram scale. To demonstrate the practicability of this reaction, two bioactive compound skeletons were synthesized in good yields. This method can also be used to late-stage modification of curcumin.

Iodine-Mediated Synthesis of Aromatic Thioethers with Aromatic Amines and Sulfonyl Hydrazides in High Regioselectivity via C(sp2)-H Bond Functionalization

An iodine-mediated synthesis of aromatic thioethers from aromatic amines and sulfonyl hydrazides via C(sp2)-H bond functionalization and C-S bond formation has been developed. In this procedure, various substituents on the sulfonyl hydrazides, such as alkyl, methoxyl, chloro, bromo and fluoro groups, and aromatic amines are tolerated in the thiolation which generates the desired products in moderate to good yields.

DMSO/iodine-catalyzed oxidative C-Se/C-S bond formation: A regioselective synthesis of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes

A convenient metal-free and solvent-free iodine-catalyzed regioselective greener protocol to access different types of unsymmetrical chalcogenides with nitrogen- or oxygen-containing arenes through oxidative C-Se/C-S formation via direct C(sp2)-H bond activation was developed. The products were obtained in good to excellent yields using [O or N]-containing arenes, half equiv. of various odorless diorganyl dichalcogenides (S/Se), iodine (20 mol%) as the catalyst and 3 equiv. of DMSO as the oxidant, applying MW irradiation for 10 min.

Iodine-mediated thiolation of phenol/phenylamine derivatives and sodium arylsulfinates in neat water

An efficient and convenient protocol for iodine-mediated thiolation of phenols/phenylamines with sodium benzene-sulfinates in water has been achieved. In this transformation, environment-friendly conditions (including metal-free and water as solvent) are employed under air conditions, and a series of valuable thioethers are easily obtained in moderate to good yields.

Iodine catalyzed cross-dehydrogenative C-S coupling by C(sp2)-H bond activation: Direct access to aryl sulfides from aryl thiols

A novel, efficient and unprecedented green protocol for the formation of C-S bonds has been developed under metal-free conditions. This protocol involves the synthesis of aryl sulfides through the cross-dehydrogenative coupling of readily available aryl t