- S-(Trifluoromethyl)Benzothioate (TFBT): A KF-Based Reagent for Nucleophilic Trifluoromethylthiolation
-
S-(Trifluoromethyl)benzothioate (TFBT) has been developed as an inexpensive, bench-stable, and user-friendly trifluoromethylthiolation reagent, which can be easily synthesized by using KF as the only fluorine source. By using TFBT, trifluoromethylthiolates with various counterions can be readily obtained. The synthetic application of TFBT was demonstrated by trifluoromethylthiolation-halogenation of arynes, bis(trifluoromethylthiolation)–halogenation of 1,2-benzdiynes, nucleophilic substitution of alkyl halides, deoxytrifluoromethylthiolation of alcohols, and cross-coupling with aryl and vinyl boronic acids.
- Meng, Depei,Lyu, Yichong,Ni, Chuanfa,Zhou, Min,Li, Yang,Hu, Jinbo
-
-
- Silver-Mediated Trifluoromethylthiolation-Iodination of Arynes
-
(Chemical Equation Presented). A one-pot trifluoromethylthiolation-iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii-Umemoto-type electrophilic trifluoromethylation reagents.
- Zeng, Yuwen,Hu, Jinbo
-
supporting information
p. 856 - 859
(2016/03/04)
-
- Direct catalytic trifluoromethylthiolation of boronic acids and alkynes employing electrophilic shelf-stable N-(trifluoromethylthio)phthalimide
-
A new and safe method for the synthesis of N-(trifluoromethylthio) phthalimide, a convenient and shelf-stable reagent for the direct trifluoromethylthiolation, has been developed. N-(Trifluoromethylthio) phthalimide can be used as an electrophilic source of F3CS + and reacts readily with boronic acids and alkynes under copper catalysis. The utility of CF3S-containing molecules as biologically active agents, the mild reaction conditions employed, and the high tolerance of functional groups demonstrate the potential of this new methodology to be widely applied in organic synthesis as well as industrial pharmaceutical and agrochemical research and development. Shelf life: A new and safe method for the synthesis of N-(trifluoromethylthio)phthalimide has been developed. It serves as a convenient and shelf-stable reagent for the direct copper-catalyzed trifluoromethylthiolation of readily available boronic acids and alkynes. Copyright
- Pluta, Roman,Nikolaienko, Pavlo,Rueping, Magnus
-
supporting information
p. 1650 - 1653
(2014/03/21)
-