42881-80-1

Upstream product

• 1135-14-4 4-aminophenyl phenyl sulfide 
• 51787-20-3 N,N-dimethyl-4-(phenylsulfinyl)aniline 
• 121-69-7 N,N-dimethyl-aniline 
• 931-59-9 benzenesulfenyl chloride 
• 591-50-4 iodobenzene 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 
• 194720-38-2 2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 169216-70-0 4-Benzenesulfinyl-2,3,5,6-tetramethyl-phenol 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 98-80-6 phenylboronic acid 
• 80-17-1 benzenesufonyl hydrazide 

Downstream Products

• 62291-62-7 N,N-dimethyl-4-(benzylthio)benzenamine 

Relevant academic research and scientific papers

Cobalt-catalyzed aryl-sulfur bond formation

A new cobalt-catalyzed coupling of aryl halides with thiophenols and alkanethiols is reported. A variety of aryl sulfides can be prepared in excellent yields under mild reaction conditions using 1-2 mol % of Col2(dppe) and Zn. This new cobalt-catalyzed coupling represents an interesting addition to previously known methods to synthesize thioethers.

Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators

Many reactions catalyzed by Pd complexes with N-heterocyclic carbene (NHC) ligands are performed in the presence of amines which usually act as coupling reagents or mild bases. However, amines can react with Pd/NHC complexes in a number of ways: enhancing molecular catalysis, causing the catalyst deactivation or triggering the ligandless modes of catalysis by producing NHC-free active palladium species. This study gains insight into conditions required for the efficient use of amines as activators of molecular Pd/NHC catalysis and preventing the undesirable reductive cleavage of the Pd-NHC bond in catalytic systems. Reactions of Pd/NHC complexes with various amines within a temperature range of 25-140 °C and thermal stability of the resulting amino-complexes are examined. The results indicate the major influence of the amine structure and reaction temperature on the catalyst transformation. In particular, thermal decomposition of Pd/NHC complexes with aliphatic amine ligands predominantly leads to reductive Pd-NHC bond cleavage, while deprotonation of the complexes with primary and secondary aliphatic amine ligands in the presence of strong bases at 25-60 °C promotes the activation of molecular Pd/NHC catalysis. Efficient Pd-PEPPSI complex-amine systems suitable for strong-base-promoted C-S cross-coupling reactions between aryl halides and thiols are suggested on the basis of these findings.

Multicomponent Synthesis of Sulfones and Sulfides from Triarylbismuthines and Sodium Metabisulfite in Deep Eutectic Solvents

This study describes a novel and catalyst-free methodology for the multicomponent synthesis of a broad range of sulfones, disulfides, and sulfides from non-toxic triarylbismuthines (Ar3Bi) and sodium metabisulfite (Na2S2O5) in deep eutectic solvents (DESs). The fine tuning of the DESs properties allowed the solubility of all reagents, enhancing their reactivity, as well as, the recyclability of the reaction medium for at least 5 consecutive cycles. Thus, this versatile strategy uses non-toxic reagents without the need of metal catalysts in a sustainable solvent, being an interesting alternative to traditional hazardous protocols.

Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5–10 % Cu(OAc)2?H2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrop

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.

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.

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 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.

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