351-60-0Relevant articles and documents
A convenient method for the transformation of alcohols into alkyl trifluoromethyl sulfides
Kolomeitsev,Chabanenko,Roschenthaler,Yagupolskii
, p. 145 - 146 (1994)
Alkyl trifluoromethyl sulfides are prepared by phosphitylation of alcohols or α-hydroxy esters using bis(diethylamido)chlorophosphite followed by the reaction with bis(trifluoromethyl) disulfide under extremely mild conditions in near by quantitative yields.
Trifluoromethyl Sulfoxides: Reagents for Metal-Free C?H Trifluoromethylthiolation
Carlton, C. Grace,McDouall, Joseph J. W.,Perry, Gregory J. P.,Procter, David J.,Tayu, Masanori,Wang, Dong
supporting information, p. 15918 - 15922 (2020/07/20)
Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C?H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.
Fluoroalkylselenolation of Alkyl Silanes/Trifluoroborates under Metal-Free Visible-Light Photoredox Catalysis
Ghiazza, Clément,Khrouz, Lhoussain,Billard, Thierry,Monnereau, Cyrille,Tlili, Anis
supporting information, p. 1559 - 1566 (2019/11/03)
Herein a metal-free fluoroalkylselenolation of alkylsilanes as well as potassium alkyltrifluoroborates under visible light photocatalysis is disclosed. The developed methodologies are performed under mild conditions, room temperature in the presence of an organic photocatalyst and blue LED irradiation. Mechanistic investigations including luminescence and EPR spectroscopy allow us to shed light on both mechanisms.
Ir(III)-Catalyzed mono-olefination of Aryl C-H Bonds Using -SCF3 as a Weak directing group
Bao, Rui-Peng,Chen, Xian,Li, Chen,Wang, Dong-Hui
supporting information, p. 8116 - 8121 (2019/10/14)
The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2′-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.
