137170-74-2

Upstream product

• 5535-48-8 PVS 
• 80859-83-2 1-benzene 
• 103698-35-7 2-(1-adamantyl)-1-phenylsulphonyl-1-(pyridine-2-thiyl)ethane 
• 281-23-2 adamantane 
• 963-16-6 (E)-1,2-bis(phenylsulfonyl)ethylene 
• 828-51-3 1-Adamantanecarboxylic acid 

Relevant academic research and scientific papers

Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp3)-H Bonds and Aliphatic Carboxylic Acids

Intermolecular functionalization of C(sp3)-H bonds and aliphatic carboxylic acids enables the efficient synthesis of high value-added organic compounds from readily available starting materials. Although methods involving hydrogen atom transfer have been developed for such functionalization, these methods either work for only activated C(sp3)-H bonds or bring in a narrow set of functional groups. Here we describe a Cu-catalyzed process for the diverse functionalization of both unactivated C(sp3)-H bonds and aliphatic carboxylic acids. The process is enabled by the trapping of alkyl radicals generated through hydrogen atom abstraction by arylsulfonyl-based SOMO-philes, which introduces a large array of C, N, S, Se, and halide-based functional groups. The chemoselectivity can be switched from C-H functionalization to decarboxylative functionalization by matching the bond dissociation energy of the hydrogen atom transfer reagent with that of the target C-H or O-H bond.

Reductive Addition to Electron-deficient Olefins with Trivalent Iodine Compounds

(Diacyloxyiodo)arene was treated with electron-deficient olefins in the presence of hydrogen donor such as 1,4-cyclohexadiene to give the reductive addition products via alkyl radical through the radical decarboxylative pathway in good yields.Moreover, this system was able to generate either alkoxycarbonyl radicals or alkyl radicals with benzene, which was prepared from alcohol, oxalyl chloride, and (diacetoxyiodo)benzene via two steps, depending on reaction conditions.These radicals were also utilized for C-C bond formation with electron-deficient olefins.

Reductive Addition of Alkyl Radical to Phenyl Vinyl Sulfone

Radicals generated from (diacyloxyiodo)benzene readily added to phenyl vinyl sulfone to give 2-alkylethyl phenyl sulfone in the presence of a hydrogen donor such as 1,4-cyclohexadiene, 1,3-dioxolane, or triethylsilane.Among these donors, 1,4-cyclohexadien

Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones

Irradiation of O-acyl derivatives 1 of N-hydroxy-2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.

SOME FURTHER NOVEL TRANSFORMATIONS OF GEMINAL (PYRIDINE-2-THIYL) PHENYLSULPHONES

Geminal (pyridine-2-thiyl) phenylsulphones, obtained by decarboxylative radical addition of O-acyl derivatives of N-hydroxy-2-thiopyridone onto phenyl vinyl sulphone, undergo a wide variety of further transformations when subjected to sodium telluride or to organoaluminum reagents.

RADICAL ADDITION TO VINYL SULPHONES AND VINYL PHOSPHONIUM SALTS

Alkyl radicals, derived from decarboxylation of carboxylic acids, add readily to phenyl vinyl sulphone and vinyl phosphonium bromide.The adducts may be further converted into a variety of useful synthetic intermediates.