372-64-5Relevant articles and documents
Dear,Gilbert
, p. 310 (1972)
Haas,Peach
, p. 299,302 (1965)
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.).
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Henn,Sundermeyer,Witz,Pritzkow
, p. 225 - 238 (1989)
2-Chloro-1,1,2,3,3,4,4,-heptafluoro-1,3-dithietane (7b), 2,4-dichloro-1,1,2,3,3,4-hexafluoro-1,3-dithietane (7c), 2-chloro-1,1,2,4,4-pentafluoro-3,3-dioxo-1,3-dithietane (9b), 2,4-dichloro-1,1,2,4-tetrafluoro-3,3-dioxo-1,3-dithietane (9c), and 1,1,2,2,4,4
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.