97992-89-7

Upstream product

• 135-19-3 β-naphthol 
• 931-59-9 benzenesulfenyl chloride 
• 573-97-7 1-bromo-2-naphthol 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 3857-83-8 2-naphthyl triflate 
• 14204-24-1 N-(phenylthio)succinimide 
• 831-91-4 Benzyl phenyl sulfide 
• 873-55-2 sodium benzenesulfonate 
• 80-17-1 benzenesufonyl hydrazide 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 108979-03-9 (2-methoxynaphthalen-1-yl)(phenyl)sulfane 
• 108980-58-1 1-benzenesulfonyl-2-methoxy-naphthalene 

Relevant academic research and scientific papers

Mechanistic Investigation of a Synthetic Route to Biaryls by the Sigmatropic Rearrangement of Arylsulfonium Species

A comprehensive mechanistic investigation was conducted on the coupling reaction of aryl sulfoxides with phenols by using trifluoroacetic anhydride to yield biaryls. NMR experiments revealed that our previously proposed mechanism, which consists of a cascade of an interrupted Pummerer reaction and a rate-determining [3,3] sigmatropic rearrangement, is reasonable. The electronic effects of the substrates were also evaluated to elucidate the nature of the rearrangement step. Based on experimental observations and theoretical calculations, we conclude that the rearrangement is highly asynchronous and stepwise rather than concerted when electron-rich phenols are employed for the reaction.

Chalcogenylation of Naphthalene Derivatives Catalyzed by Iron(III) Chloride and Potassium Iodide

We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl 3and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2

Regioselective Ortho‐C–H sulfenylation of free phenols catalyzed by Co(II)-immobilized on silica-coated magnetic nanoparticles

Fe3O4?SiO2-UT?CoII is prepared by the silica-coated magnetic nanoparticles, urea-triazole, and CoCl2. This organic-inorganic hybride composite showed a good to excellent catalytic activity toward regioselective ortho-sulfenylation of free phenols and naphthols using pivalic anhydride as a directing group, also K2S2O8 and PPh3 were employed as oxidant and additive respectively. The newly synthesized catalyst was fully characterized by using different techniques such as FT-IR, TGA, DTG, TEM, SEM, EDS, ICP and VSM analyses. The competitive price, accessibility and lower toxicity of cobalt compared to expensive transition metals using for C–H bond activation and functionalization constitute precious advantages for this method. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its catalytic activity after five cycles.

TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME

An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.

Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot

Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.

Co(II)-catalyzed regioselective clean and smooth synthesis of 2-(aryl/alkyl-thio)phenols via sp2 C-H bond activation

The first example of a smooth, practical and useful strategy for the preparation of ortho-aryl/alkyl sulfenyl phenols by using the reaction of aryl/alkyl thiols with phenols in the presence cobalt as catalyst, and with the assistance of acetic anhydride as directing group via C-H bond activation, was developed. Described method enables to form selectively C-S bond without any ligand, oxidant, and aryl/alkyl halide under mild conditions.

Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Synthesis of Aryl Sulfides in Water

An environmentally benign method for the synthesis of aryl sulfides in water under mild conditions has been realized, in which arenes are coupled with equal stoichiometry of allyl sulfides. This arylthiolation is enabled by the presence of the Lipshutz su

Iodine-mediated sulfenylation of 4-hydroxycoumarins with sulfonyl hydrazides under aqueous conditions

An efficient, metal-free approach to the synthesis of sulfenylated coumarins based on the iodine catalyzed regioselective sulfenylation of 4-hydroxycoumarins with arylsulfonyl hydrazides was developed under mild conditions in water. Various sulfenylated c

Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C?S Bond Formation: Scope and Mechanistic Studies

A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C?S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.

Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media

A convenient and novel approach has been developed for the synthesis of unsymmetrical diaryl sulfides by the reaction of sulfonyl hydrazides with phenols using a [Bmim][Br] ionic liquid through the formation of C-S bonds. The reaction has further been extended to indole, β-naphthol and aromatic amine moieties. This protocol offers a new, versatile and greener approach for thiolation of natural phenols (monoterpenes)/aromatic phenols/β-naphthols/aromatic amines and indoles without using any catalyst. A broad range of functional groups were well tolerated in this reaction system.