Chan–Lam-Type C–S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
نویسندگان
چکیده
A Chan–Lam-type C–S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up 92% yields the presence of a copper catalyst and potassium sulfite. Both electron-rich electron-poor diverse organoboron compounds were tolerated for synthesis heteroaryl dithioethers. The mechanistic study suggested that sulfite was involved deoxygenation sulfinate through radical process.
منابع مشابه
Cross-Coupling Reaction of Organoboron Compounds via Base-Assisted Transmetalation to Palladium(II) Complexes
Until recently, organoboronic acids have been of limited use in organic synthesis due to their low reactivity for ionic reactions. During the past two decades; however, it has become increasingly clear that they are valuable reagents capable of undergoing many carbon-carbon bond formations in organic syntheses. In 1979, catalytic carbon-carbon bond formation, via transmetalation between organob...
متن کاملCu-catalyzed cross-coupling reactions of epoxides with organoboron compounds.
A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to β-phenethyl alcohols, which are valuable synthetic intermediates.
متن کاملPyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides.
Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in react...
متن کاملElectrochemical hydroxylation of organoboron compounds.
Cathodic hydroxylation of organoboron compounds was successfully performed under an oxygen atmosphere, producing the corresponding phenol derivatives with high selectivity and efficiency.
متن کاملDecarbonylative organoboron cross-coupling of esters by nickel catalysis
The Suzuki-Miyaura cross-coupling is a metal-catalysed reaction in which boron-based nucleophiles and halide-based electrophiles are reacted to form a single molecule. This is one of the most reliable tools in synthetic chemistry, and is extensively used in the synthesis of pharmaceuticals, agrochemicals and organic materials. Herein, we report a significant advance in the choice of electrophil...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Organic Letters
سال: 2021
ISSN: ['1523-7060', '1523-7052']
DOI: https://doi.org/10.1021/acs.orglett.1c02299