145326-60-9Relevant academic research and scientific papers
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.
Pd-Catalyzed Difluoromethylthiolation of Aryl Chlorides, Bromides and Triflates
Wu, Jiang,Lu, Changhui,Lu, Long,Shen, Qilong
supporting information, p. 1031 - 1034 (2018/09/25)
A highly efficient Pd-catalyzed difluoromethylthiolation of aryl chlorides, bromides and triflates is described. A variety of aryl halides with common functional groups were difluoromethylthiolated in moderate to excellent yields. Furthermore, several nat
PhSO2SCF2H: A Shelf-Stable, Easily Scalable Reagent for Radical Difluoromethylthiolation
Zhu, Dianhu,Shao, Xinxin,Hong, Xin,Lu, Long,Shen, Qilong
supporting information, p. 15807 - 15811 (2016/12/16)
A new shelf-stable and easily scalable difluoromethylthiolating reagent S-(difluoromethyl) benzenesulfonothioate (PhSO2SCF2H) was developed. PhSO2SCF2H is a powerful reagent for radical difluoromethylthiolation of aryl and alkyl boronic acids, decarboxylative difluoromethylthiolation of aliphatic acids, and a phenylsulfonyl-difluoromethylthio difunctionalization of alkenes under mild reaction conditions.
N-Difluoromethylthiophthalimide: A Shelf-Stable, Electrophilic Reagent for Difluoromethylthiolation
Zhu, Dianhu,Gu, Yang,Lu, Long,Shen, Qilong
supporting information, p. 10547 - 10553 (2015/09/28)
A new, electrophilic difluoromethylthiolating reagent N-difluoromethylthiophthalimide 3 was developed. Reagent 3 can be readily synthesized in four steps from easily available starting materials phthalimide and TMSCF2H. N-difluoromethylthiophthalimide 3 is a powerful electrophilic difluoromethylthiolating reagent that allows the difluoromethylthiolation of a wide range of nucleophiles including aryl/vinyl boronic acids, alkynes, amines, thiols, β-ketoesters, and oxindoles and electron-rich heteroarenes such as indole, pyrrole, 1H-pyrrolo[2,3-b]pyridine, imidazo[1,2-a]pyridine, aminothiazole, isoxazole, and pyrazole under mild conditions.
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.
Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ
Bayarmagnai, Bilguun,Matheis, Christian,Jouvin, Kvin,Goossen, Lukas J.
, p. 5753 - 5756 (2015/06/10)
A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups - a largely unexplored substituent with highly promising properties - into drug-like molecules. A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts.
Synthesis and reactivity of α-bromo-4-(difluoromethylthio) acetophenone
Demchenko,Nazarenko,Andrushko,Fediyuk,Krasovsky,Yagupolsky
, p. 965 - 969 (2007/10/03)
A synthesis is reported for α-bromo-4-difluoromethylthioacetophenone and the conditions for the condensation of this compound with 2-aminothiazole, 2-amino-5-chloropyridine, 2-amino-4,5-dihydro-3H-pyrrole, benzimidazoline-2- thione, oxadiazoline-2-thione, and thiourea were studied. S- and N-substituted azaheterocycles containing the 4-(difluoromethylthio)phenyl fragment were synthesized and characterized.
