1584705-82-7Relevant academic research and scientific papers
Exploration of the Synthetic Potential of Electrophilic Trifluoromethylthiolating and Difluoromethylthiolating Reagents
Zhang, Jingjing,Yang, Jin-Dong,Zheng, Hanliang,Xue, Xiao-Song,Mayr, Herbert,Cheng, Jin-Pei
supporting information, p. 12690 - 12695 (2018/09/25)
The electrophilicity parameters (E) of some trifluoromethylthiolating and difluoromethylthiolating reagents were determined by following the kinetics of their reactions with a series of enamines and carbanions with known nucleophilicity parameters (N, sN), using the linear free-energy relationship log k2=sN(N+E). The electrophilic reactivities of these reagents cover a range of 17 orders of magnitude, with Shen and Lu's reagent 1 a being the most reactive and Billard's reagent 1 h being the least reactive electrophile. While the observed electrophilic reactivities (E) of the amido-derived trifluoromethylthiolating reagents correlate well with the calculated Gibbs energies for heterolytic cleavage of the X?SCF3 bonds (Tt+DA), the cumol-derived reagents 1 f and 1 g are more reactive than expected from the thermodynamics of the O?S cleavage. The E parameters of the tri/difluoromethylthiolating reagents derived in this work provide an ordering principle for their use in synthesis.
The trifluoromethyl-based thiophosphoro superoxyde and its preparation method (by machine translation)
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Paragraph 0144; 0145; 0146; 0147, (2016/10/17)
The invention discloses a trifluoromethyl thioperoxide and a preparation method thereof and provides a trifluoromethyl thioperoxide 2. The invention also provides a method for preparing the trifluoromethyl thioperoxide 2. The method comprises the following steps: carrying out a nucleophilic substitution reaction between ROH or ROM and a compound 1 in an organic solvent, thereby obtaining the trifluoromethyl thioperoxide 2. When the nucleophilic substitution reaction is carried out between ROH and the compound 1, the reaction needs to be carried out in the presence of an additive, wherein the additive refers to an alkaline substance or a mixture of an alkaline substance and Lewis acid. The preparation method disclosed by the invention is cheap and readily available in raw materials, simple in operation steps, mild in reaction conditions, safe to operate, low in energy consumption, environment-friendly and high in reaction yield, and the prepared product is high in purity and suitable for industrial production.
Structure-reactivity relationship of trifluoromethanesulfenates: Discovery of an electrophilic trifluoromethylthiolating reagent
Shao, Xinxin,Xu, Chunfa,Lu, Long,Shen, Qilong
, p. 3012 - 3021 (2015/03/30)
A family of electrophilic trifluoromethanesulfenates was prepared. Structure-reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities. A simplified electrophilic trifluoromethylthiolating reagent 1c was then identified that can react with a wide range of nucleophiles such as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters, oxindoles, and sodium sulfinates under mild reaction conditions. A variety of functional groups were tolerated under these conditions.
Br?sted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent
Ma, Bingqing,Shao, Xinxin,Shen, Qilong
, p. 73 - 77 (2015/03/04)
A Br?sted acid-catalyzed electrophilic trifluoromethylthiolation of indoles under mild conditions is described. The reaction was insensitive to moisture and oxygen, that should allow for easy handling. In addition, the reaction is compatible with a variety of functional groups.
N-trifluoromethylthiosaccharin: An easily accessible, shelf-stable, broadly applicable trifluoromethylthiolating reagent
Xu, Chunfa,Ma, Bingqing,Shen, Qilong
supporting information, p. 9316 - 9320,5 (2014/10/15)
A new, electrophilic trifluoromethylthiolating reagent, N-trifluoromethylthiosaccharin, was developed and can be synthesized in two steps from saccharin within 30minutes. N-trifluoromethylthiosaccharin is a powerful trifluoromethylthiolating reagent and allows the trifluoromethylthiolation of a variety of nucleophiles such as alcohols, amines, thiols, electron-rich arenes, aldehydes, ketones, acyclic β-ketoesters, and alkynes under mild reaction conditions. 'Sacch'ed out: A new, electrophilic trifluoromethylthiolating reagent, N-trifluoromethylthiosaccharin (1) can be synthesized in two steps from saccharin within 30minutes. The reagent 1 allows the trifluoromethylthiolation of a variety of nucleophiles such as alcohols, amines, thiols, electron-rich arenes, aldehydes, ketones, acyclic β-ketoesters, and alkynes under mild reaction conditions.
