78597-95-2

Upstream product

• 109-65-9 1-bromo-butane 
• 696-63-9 4-Methoxybenzenethiol 
• 109-72-8 n-butyllithium 
• 1153-43-1 4,4'-dimethoxyphenyl thiosulfonate 
• 109-79-5 n-butanethiol 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1207372-98-2 butyl 2-[2-(4-methoxyphenyl)ethynyl]benzoate 
• 104-94-9 4-methoxy-aniline 
• 109-69-3 n-Butyl chloride 
• 36651-93-1 1-((4-methoxyphenyl)diazenyl)pyrrolidine 
• 542-69-8 1-iodo-butane 
• 21130-91-6 triethoxy(4-methoxyphenyl)silane 
• 26726-20-5 sodium n-butylsulfanesulfonate 

Downstream Products

• 1077-25-4 4-hydroxyphenylbutylsulfide 
• 78597-98-5 1-(Butane-1-sulfonyl)-4-methoxy-benzene 
• 78597-97-4 1-(butylsulfinyl)-4-methoxybenzene 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 

Relevant academic research and scientific papers

Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2

An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).

Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction

A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.

Ullmann-type: N-arylation of anilines with alkyl(aryl)sulfonium salts

A palladium/copper-cocatalyzed Ullmann-type N-arylation of anilines using alkyl(aryl)sulfonium triflates as arylation reagents has been accomplished. The reaction enabled Caryl-S bond cleavage over Calkyl-S bond breakage of alkyl(aryl)sulfoniums by Pd(P(tBu)3)2/CuI and gave the corresponding N-arylated products in good to high yields. It was also significant that the reactions of aniline with asymmetric butyl(mesityl)(aryl)sulfonium triflates showed excellent selectivity, in which the aryl groups other than the bulky and electron-rich mesityl moieties were transformed.

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange

Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at ?50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.

C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes

The C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated Ni (II) N-heterocyclic carbene (NHC) complexes is investigated. Good to excellent yields can be obtained for a variety of aryl halides when using 5 mol% of the Ni (II)-NHC catalyst and 1.5 eq. of KOtBu. Both the electronic and steric effects of the NHC ligands on the catalytic performance of Ni (II)-NHC, as well as the electronic effects of aryl halides on coupling reactivity are examined. The mechanism for Ni (II)-NHC catalyzed coupling reactions is also discussed.

Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis

A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was obtained under ligand-free conditions in which disulfide generated from homocoupling could be prevented. Meanwhile, application of bidentate phosphine ligands under carbon monoxide atmosphere (CO balloon) afforded the thioester with little decomposition, which was revealed through interval NMR tracking.

A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols

A cost effective and easily available CuI/DABCO catalytic system has been developed for C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides providing excellent yields and good chemoselectivity.

Efficient reduction of sulfoxides with NaHSO3 catalyzed by I2

An efficient method for the deoxygenation of sulfoxides into their corresponding sulfides at room temperature using NaHSO3 in the presence of catalytic I2 has been reported.

COMPOSITION, SYNTHESIS, AND USE OF A NEW CLASS OF ISONITRILES

This invention relates to novel isonitriles, including arylthio isonitriles, and methods for their preparation. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.