Mild and Soft Catalyzed Trifluoromethylthiolation of Boronic Acids: The Crucial Role of Water.
The most reactive 2nd generation of trifluoromethanesulfenamides undergoes a copper-catalyzed cross-coupling reaction with boronic acids to afford CF3 S-molecules. Contrary to the previous methods in the literature, no base addition, no heating, and no large excess of reagents are required to obtain good results. Furthermore, a crucial role of a small amount of water to favor this reaction has been demonstrated. This constitutes the mildest described conditions for such a reaction.
Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Université de Lyon, Université Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622 Villeurbanne (France).
Quentin
Q
Glenadel
Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Université de Lyon, Université Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622 Villeurbanne (France).
Sébastien
S
Alazet
Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Université de Lyon, Université Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622 Villeurbanne (France).
Anis
A
Tlili
Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Université de Lyon, Université Lyon 1, CNRS, 43 Bd du 11 novembre 1918, 69622 Villeurbanne (France). thierry.billard@univ-lyon1.fr.|CERMEP - in vivo imaging Groupement Hospitalier Est, 59 Bd Pinel, 69003 Lyon (France). thierry.billard@univ-lyon1.fr.
Thierry
T
Billard
boronic acid; cross-coupling; fluorine; trifluoromethanesulfenamide; trifluoromethylthiolation