63762-91-4

Upstream product

• 15570-12-4 3-methoxybenzenethiol 
• 532-27-4 1-chloroacetophenone 
• 2388-74-1 1-methoxy-3-methylsulfanyl-benzene 
• 98-88-4 benzoyl chloride 
• 59014-89-0 bis(3-methoxyphenyl)disulfide 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 1021-45-0 phosphoric acid diethyl ester-(1-phenyl-vinyl ester) 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 16717-64-9 1-azidostyrene 
• 536-74-3 phenylacetylene 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 92014-01-2 2-phenyl-6-methoxybenzothiophene 

Relevant academic research and scientific papers

An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives

The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide.

Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Alkenyl Sulfones, Benzo[ b]thiophene 1,1-Dioxides, with Mechanistic Studies

A highly efficient catalytic system based on the cheap transition metal nickel for the asymmetric hydrogenation of challenging cyclic alkenyl sulfones, 3-substituted benzo[b]thiophene 1,1-dioxides, was first successfully developed. A series of hydrogenation products, chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides, were obtained in high yields (95-99%) with excellent enantioselectivities (90-99% ee). According to the results of nonlinear effect studies, deuterium-labeling experiments, and DFT calculation investigations, a reasonable catalytic mechanism for this nickel-catalyzed asymmetric hydrogenation was provided, which displayed that the two added hydrogen atoms of the hydrogenation products could be from H2 through the insertion of Ni-H and subsequent hydrogenolysis.

Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water

Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.

Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers

The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described.

MODULATORS OF ESTROGEN RECEPTOR PROTEOLYSIS AND ASSOCIATED METHODS OF USE

The present disclosure relates to bifunctional compounds, which find utility as modulators of estrogen receptor (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a cereblon, Von Hippel-Lindau ligase-binding moiety, Inhibitors of Apotosis Proteins, or mouse double-minute homolog 2 ligand, which binds to the respective E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Catalyst-Free Difunctionalization of Activated Alkenes in Water: Efficient Synthesis of β-Keto Sulfides and Sulfones

Difunctionalization of activated alkenes, a powerful strategy in chemical synthesis, has been accomplished for direct synthesis of a series of β-keto sulfides and β-keto sulfones. The transformation, mediated by O2, proceeds smoothly in water and without any catalyst. Prominent advantages of this method include mild reaction conditions, purification simplicity, and gram-scale synthesis, underlining the practical utility of this methodology.

A route to benzylic arylsulfoxides from β-ketosulfoxides

The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.

Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides

RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.

A facile synthesis of 3-aryl-substituted-benzothiophenes via a Lewis acid mediated cyclization of 2-arylthio-acetophenones

The boron trifluoride-etherate mediated cyclization of 2-arylthio- ketones 1a-h at ambient temperature gave 3-aryl-substituted benzothiophenes 2a-h in excellent yield. None of the rearranged 2-aryl-substituted benzothiophenes were observed.

Metallation reactions. XX. Regioselective metallation of (alkylthio)methoxybenzenes by superbases versus organolithium compounds

(Alkylthio)methoxybenzenes have been metallated using two different metallating agents. The results show that sometimes superbases and butyllithium do not functionalize the same sites. Superbases monometallate the thiomethylic carbon of meta and para (methylthio)methoxybenzenes. The same substrates on the other hand are metallated by butyllithium in ortho to the methoxy group. One-step dimetallation performed with either superbases or butyllithium occurs at the thiomethylic carbon at the aryl carbon ortho to the methoxy group. Two consecutive one-pot monometallations of the para isomer (1c) with superbases occur at the thiomethylic carbon and at the annular carbon ortho to the methoxy group, in this order. A similar procedure with butyllithium metallates the two ortho positions to the methoxy group. Monometallation of (ethylthio) derivative (1d) yields, products substituted in ortho to the methoxy group using, either superbases or butyllithium. Dimetallation of this compound always substitutes the hydrogen ortho to the methoxy group and a thiomethylenic hydrogen.