Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides

Abstract

For Abstract see ChemInform Abstract in Full Text.

Arylsulfur trifluorides: Improved method of synthesis and use as in situ deoxofluorination reagents

“…Thus, if simpler arylsulfur trifluorides were to exhibit similar in situ reactivity, the lower cost of such reagents might then make them preferred over Fluolead for an in situ process. Phenyl and mesityl disulfides are readily available, either commercially or from reduction of the respective sulfonylchlorides [23], and our Br 2 / KF process proved successful for conversion of each to its respective ArSF 3 reagent (>70% yields for each).…”

Electron-catalyzed radical perfluoroalkylation of organic sulfides: the serendipitous use of the TMEDA/I2 complex as a radical initiator

“…Electrophilic perfluoroalkyl radicals R F derived from R F -I have recently been informed to functionalize sulfide RSH residues very efficiently [6] , when the reactions are initiated by visible light and a metal-photocatalyst in the presence of N,N,N´,N´-tetramethylethylene diamine, TMEDA, in MeCN as solvent. In the past, the perfluoroalkylation of sulfides has been accomplished by different methods under diverse reaction conditions, [4], [7], [8], [9], [10], [11], [12] such as those indicated in Scheme 1. Inspired by the results of Noel and collaborators [6] for the perfluoroalkylation of cysteine derivatives employing TMEDA, R F -I and a transition metal photoorganocatalyst, we replaced our reported strategy for the radical perfluoroalkylation reactions using Cs 2 CO 3 [13] for TMEDA and used a commercial fluorescent light CFL in the absence of an organophotocatalyst (POC).…”