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Difluoro(aryl)(perfluoroalkyl)‐λ 4 ‐sulfanes and Selanes: Missing Links of Trichloroisocyanuric Acid/Potassium Fluoride Chemistry
Author(s) -
Brüning Fabian,
Pitts Cody Ross,
Kalim Jorna,
Bornemann Dustin,
Ghiazza Clément,
Montmollin Jean,
Trapp Nils,
Billard Thierry,
Togni Antonio
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201910594
Subject(s) - chemistry , aryl , oxidative addition , reactivity (psychology) , heteroatom , reagent , chalcogen , organic chemistry , fluoride , combinatorial chemistry , medicinal chemistry , inorganic chemistry , alkyl , medicine , ring (chemistry) , alternative medicine , pathology , catalysis
The TCICA/KF approach to oxidative fluorination of heteroatoms has emerged as a surprisingly simple, safe, and versatile surrogate to classically challenging fluorination reactions. Although polyfluorination (or chlorofluorination) of diaryl disulfides, diaryl diselenides, diaryl ditellurides, aryl iodides, and aryl(perfluoroalkyl)tellanes has been described, the application of this TCICA/KF methodology to aryl(perfluoroalkyl)sulfanes and selanes remains an area of unexplored chemical space. Accordingly, to address the “missing links” in the developing series of chalcogen‐based substrate reactivity, we report mild syntheses of metastable difluoro(aryl)(perfluoroalkyl)‐λ 4 ‐sulfanes and selanes. As only limited examples of these species exist in the current literature (accessible only by using F 2 or XeF 2 /HF), we have carried out detailed structural analyses, primarily using NMR and SC‐XRD data. In addition, we investigate the effect of the perfluoroalkyl chain on the outcome of oxidative fluorination, and, finally, we provide preliminary evidence that difluoro(aryl)(trifluoro‐methyl)‐λ 4 ‐sulfanes may act as fluorinating reagents.