- Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide
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A method for facile difluoromethylation of various thiols using (difluoromethyl)triphenylphosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium labeling experiments and cyclic voltammetry measurements reveal that the difluoromethylation occurs via a SRN1-type mechanism. Substrate scope is broad, and various functional groups are tolerated (OH, NH2, amide, ester).
- Heine, Niklas B.,Studer, Armido
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supporting information
p. 4150 - 4153
(2017/08/14)
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- A Route to α-Fluoroalkyl Sulfides from α-Fluorodiaroylmethanes
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α,α-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating α-thioaryl-α,α-difluoroacetophenones (Ar1COCF2SAr) and difluoromethylthiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature. The method has also been extended to the synthesis of α-thioaryl-α-monofluoroacetophenones using α-monofluorodibenzoylmethane. Moreover, the benzoyl cation derived from α,α-difluorodibenzoylmethane can react with nucleophiles to afford the desired products in a one-pot process.
- Lin, Ya-Mei,Yi, Wen-Bin,Shen, Wan-Zhao,Lu, Guo-Ping
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supporting information
p. 592 - 595
(2016/02/18)
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- Direct S-difluoromethylation of thiols using the Ruppert-Prakash reagent Dedicated to Prof. Veronique Gouverneur on the occasion of receiving the ACS Award for Creative Work in Fluorine Chemistry.
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Direct S-difluoromethylation of aryl and aliphatic thiols using the Ruppert-Prakash reagent is demonstrated. The reaction produces trimethylsilyldifluoromethyl sulfides, which upon cleavage with fluoride produces the difluoromethyl sulfides. The key reaction features are the use of relatively inexpensive and commercially available starting materials, shorter reaction times, ambient temperatures, easy reaction procedure, and selective S-difluoromethylation in the presence of -OH, -NH2 and -CO2H functional groups. Furthermore, one-pot arylthiodifluoromethyl transfer to PhCHO is also demonstrated.
- Prakash, G.K. Surya,Krishnamoorthy, Sankarganesh,Kar, Sayan,Olah, George A.
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p. 186 - 191
(2015/10/28)
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- 3-(p-Alkylsulfonylphenyl)oxazolidinone derivatives as antibacterial agents
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This invention relates to novel 3-(p-alkylsulfonylphenyl)oxazolidinone derivatives, pharmaceutical compositions containing them and methods of using them to alleviate bacterial infections in mammals.
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