51679-54-0Relevant academic research and scientific papers
Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H
Howard, Joseph L.,Schotten, Christiane,Alston, Stephen T.,Browne, Duncan L.
, p. 8448 - 8451 (2016)
We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl-SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.
Visible light-promoted difluoromethylthiolation of aryldiazonium salts
Wang, Wengui,Zhang, Shuxiang,Zhao, Huaiqing,Wang, Shoufeng
, p. 8565 - 8568 (2018/11/27)
Difluoromethylthiolation of aryldiazonium salts under photocatalytic conditions with a shelf-stable, easily prepared and inexpensive reagent, PhSO2SCF2H was described. A variety of difluoromethylthioethers were obtained utilizing aryldiazonium salts containing different functional groups. Aryldiazonium salts with a heteroarene moiety were tolerated. Fluorescence quenching experiments indicated that both oxidative and reductive quenching cycles occurred during this process.
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.
Prakash, G.K. Surya,Krishnamoorthy, Sankarganesh,Kar, Sayan,Olah, George A.
, p. 186 - 191 (2015/10/28)
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.
Copper-promoted sandmeyer difluoromethylthiolation of aryl and heteroaryl diazonium salts
Wu, Jiang,Gu, Yang,Leng, Xuebing,Shen, Qilong
supporting information, p. 7648 - 7652 (2015/06/25)
An efficient copper-promoted difluoromethylthiolation of aryl and heteroaryl diazonium salts is described. The reaction is conducted under mild reaction conditions and various functional groups were compatible. In addition, reactions of heteroaryl diazonium salts such as pyridyl, quinolinyl, benzothiazolyl, thiophenyl, carbazolyl, and pyrazolyl diazonium salts occurred smoothly to afford the medicinally important difluoromethylthiolated heteroarenes. Furthermore, a more practical one-pot direct diazotization and difluoromethylthiolation protocol was developed, and it converts the aniline derivatives into difluoromethylthiolated arenes. The utility of the method is demonstrated by difluoromethylthiolation of a number of natural products and drug molecules. A dose of salt: The title reaction is conducted under mild reaction conditions and various functional groups are compatible. (Hetero)aryl diazonium salts reacted smoothly to afford the medicinally important difluoromethylthiolated (hetero)arenes. A practical one-pot direct diazotization and difluoromethylthiolation protocol was developed for aniline derivatives to generate difluoromethylthiolated arenes.
New electrophilic difluoromethylating reagent
Surya Prakash,Weber, Csaba,Chacko, Sujith,Olah, George A.
, p. 1863 - 1866 (2008/02/04)
A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.
