34678-74-5

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Synthesis Reference(s)

Synthetic Communications, 5, p. 173, 1975 DOI: 10.1080/00397917508064105

Upstream product

• 576-83-0 2,4,6-trimethylphenyl bromide 
• 103-19-5 di(p-tolyl) disulfide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 106-45-6 para-thiocresol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 933-00-6 p-methylbenzenesulfenyl chloride 

Relevant academic research and scientific papers

Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide

Thiol Activation toward Selective Thiolation of Aromatic C-H Bond

Direct C-S bond coupling is an attractive way to construct aryl sulfur ether, a building block for a variety of biological active molecules. Herein, we disclose an effective model for regioselective thiolation of the aromatic C-H bond by thiol activation instead of arene activation. Strikingly, this method has been applied into anisole derivatives that are not available in the arene activation approach to forge a single thioether isomer with high reactivity.

Iodine(III) Enabled Dehydrogenative Aryl C?S Coupling by in situ Generated Sulfenium Ion

Due to the normal polarity preferences, arenes form stable complexes with thiols through S?H???π interaction and direct dehydrogenative aryl C?S coupling is usually restricted. We report here an umpolung based one pot and direct C?S coupling approach unde

Cu-catalyzed direct C-H thiolation of electron-rich arenes with arylsulfonyl hydrazides

An efficient Cu-catalyzed direct C–H thiolation of electron-rich arenes with arylsulfonyl hydrazides has been developed. Various mono(or bis)-thioether products were obtained in moderate to good yields. Mechanistic studies suggest that the reaction likely proceeds through free-radical formation including arylthio radical and sulfonyl radical, while both disulfanes and sulfonothioates are the major thiolation species in this transformation.

Lewis Base/Bronsted Acid Dual-Catalytic C-H Sulfenylation of Aromatics

A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.

Thieme Chemistry Journals Awardees - Where Are They Now?Molybdenum(V)-Mediated Synthesis of Nonsymmetric Diaryl and Aryl Alkyl Chalcogenides

Oxidative chalcogenation reaction using molybdenum(V) reagents provides fast access to a wide range of nonsymmetric aryl sulfides and selenides. The established protocol is tolerated by a variety of labile functions, protecting groups, and aromatic heterocycles. In particular, when labile moieties are present, the use of molybdenum(V) reagents provides superior yields compared to other oxidants.

Iodine-catalyzed thiolation of electron-rich aromatics using sulfonyl hydrazides as sulfenylation reagents

Iodine-catalyzed thiolation of electron-rich aromatics, including substituted anisole, thioanisole, phenol, toluene, and naphthalene, using sulfonyl hydrazides as sulfenylation reagents was carried out. Sulfonothioates, the products of decomposition of sulfonyl hydrazides in the presence of iodine, are proposed as the major sulfenylation species in this transformation.

Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes

A simple, efficient, and practical metal-free C-H sulfenylation of substituted electron-rich arenes has been developed. This method is highly regioselective, and the corresponding aryl sulfides were obtained in moderate to excellent yields from stable and

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers

A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).

Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes

A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.