372-64-5Relevant articles and documents
Ag-Mediated Trifluoromethylthiolation of Inert Csp3-H Bond
Zhao, Yue,Lin, Jin-Hong,Hang, Xiao-Chun,Xiao, Ji-Chang
, p. 14120 - 14125 (2018)
Ag-mediated trifluoromethylthiolation of inert Csp3-H bond with CF3SOCl is described. Widely available reagents and operational simplicity make this protocol attractive.
Boron Trifluoride-Mediated Trifluoromethylthiolation of N-Acyliminiums
Maury, Julien,Force, Guillaume,Darses, Benjamin,Leb?uf, David
, p. 2752 - 2756 (2018)
Herein, we describe a hitherto unprecedented trifluoromethylthiolation of N-acyliminiums promoted by boron trifluoride etherate to enable a convenient access to various α-amino trifluoromethylthiolate derivatives in good yields. The reaction proceeds under mild conditions, relying on copper(I) trifluoromethylthiolate as a nucleophilic partner. (Figure presented.).
Copper-Catalyzed Domino Cyclization/Trifluoromethylthiolation of Unactivated Alkenes: Access to SCF3-Containing Pyrrolines
Guo, Kang,Zhang, Honglin,Cao, Shujun,Gu, Chen,Zhou, Huating,Li, Jie,Zhu, Yingguang
, p. 2261 - 2264 (2018)
A novel and efficient copper-catalyzed cascade cyclization/trifluoromethylthiolation of unactivated olefins has been achieved with the stable and readily available AgSCF3 as the SCF3 source. A range of SCF3-substituted pyr
A plasma synthesis for the perfluoroalkyl di-, tri-, and tetrasulfides: Reaction of trifluoromethyl radicals with sulfur vapor
Yasumura, Takashi,Lagow, Richard J.
, p. 3108 - 3110 (1978)
A new synthesis for a number of perfluoroalkyl di-, tri-, and tetrasulfides (CF3SnCF3, C2F5SnCF3, C2F5SnC2F5, n = 2-4) has been developed using a low-temperature glow discharge to dissociate sulfur vapor and generate trifluoromethyl radicals from hexafluoroethane. These compounds were characterized by mass spectra, infrared spectra, and NMR spectra.
Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization
Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
, p. 389 - 392 (2020/03/04)
3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.
Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation
Lipp, Alexander,Badir, Shorouk O.,Dykstra, Ryan,Gutierrez, Osvaldo,Molander, Gary A.
supporting information, p. 3507 - 3520 (2021/06/11)
A catalyst- and additive-free decarbonylative trifluoromethylthiolation of aldehyde feedstocks has been developed. This operationally simple, scalable, and open-to-air transformation is driven by the selective photoexcitation of electron donor-acceptor (EDA) complexes, stemming from the association of 1,4-dihydropyridines (donor) with N-(trifluoromethylthio)phthalimide (acceptor), to trigger intermolecular single-electron transfer events under ambient- and visible light-promoted conditions. Extension to other electron acceptors enables the synthesis of thiocyanates and thioesters, as well as the difunctionalization of [1.1.1]propellane. The mechanistic intricacies of this photochemical paradigm are elucidated through a combination of experimental efforts and high-level quantum mechanical calculations [dispersion-corrected (U)DFT, DLPNO-CCSD(T), and TD-DFT]. This comprehensive study highlights the necessity for EDA complexation for efficient alkyl radical generation. Computation of subsequent ground state pathways reveals that SH2 addition of the alkyl radical to the intermediate radical EDA complex is extremely exergonic and results in a charge transfer event from the dihydropyridine donor to the N-(trifluoromethylthio)phthalimide acceptor of the EDA complex. Experimental and computational results further suggest that product formation also occurs via SH2 reaction of alkyl radicals with 1,2-bis(trifluoromethyl)disulfane, generated in-situ through combination of thiyl radicals. (Figure presented.).
Trifluoromethylthiolation and trifluoromethanesulfonylation of β,γ-unsaturated hydrazones
Xiao, Hongqing,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
, (2020/04/27)
The trifluoromethylthiolation and trifluoromethanesulfonylation of β,γ-unsaturated hydrazones was accomplished with silver(I) trifluoromethanethiolate (AgSCF3) as a CF3S source and sodium trifluoromethylsulfinate (CF3SO2Na) as a CF3SO2 source, respectively. These general methods for the preparation of dihydropyrazoles containing CF3S or CF3SO2 groups were characterized by mild reaction conditions and good functional group tolerance.
Hydrotrifluoromethylthiolation of Unactivated Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride through Deoxygenative Reduction and Photoredox Radical Processes
Ouyang, Yao,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 18508 - 18512 (2019/11/14)
An ongoing challenge in trifluoromethylthiolation reactions is the use of less expensive and easily available trifluoromethylthio sources. Herein, we disclose an unprecedented usage of trifluoromethanesulfonic anhydride (Tf2O) as a radical trifluoromethylthiolating reagent. Hydrotrifluoromethylthiolation of unactivated alkenes and alkynes with Tf2O in the presence of PMePh2 and H2O under visible-light photoredox catalysis gave the addition products. The trifluoromethylthio radical (.SCF3) was first formed from Tf2O through a photoredox radical processes and deoxygenative reduction of PMePh2, and H2O serves as the H-atom donor for the hydrotrifluoromethylthiolation reaction. This reaction provides a new strategy for radical trifluoromethylthiolation.
Silver-mediated radical aryltrifluoromethylthiolation of activated alkenes by S-trifluoromethyl 4-methylbenzenesulfonothioate
Zhao, Xia,Yang, Bo,Wei, Aoqi,Sheng, Jianqiao,Tian, Miaomiao,Li, Quan,Lu, Kui
, p. 1719 - 1722 (2018/04/02)
Herein, we describe the preparation of trifluoromethylthiol-substituted oxindoles by silver-mediated aryltrifluoromethylthiolation of activated alkenes, using S-trifluoromethyl 4-methylbenzenesulfonothioate as a F3CS radical source and showing that the reagent availability, mild conditions, and broad functional group compatibility of this transformation make it a viable alternative strategy of constructing Csp3–SCF3 bonds.
TfNHNHBoc as a SCF3 source for the sulfenylation of indoles
Guo, Jing-Yu,Dai, Rui-Han,Xu, Wen-Cong,Wu, Ruo-Xin,Tian, Shi-Kai
supporting information, p. 8980 - 8982 (2018/08/21)
An unprecedented use of trifluoromethanesulfonyl hydrazides as effective SCF3 sources has been established in the sulfenylation of indoles. A range of substituted indoles participated in CuCl-catalyzed oxidative sulfenylation reaction with TfNHNHBoc in the presence of dimethyl sulfoxide to furnish structurally diverse 3-indolyl trifluoromethyl thioethers in moderate to good yields with very high regioselectivity.
