A mild, nonbasic synthesis of thioethers. The copper-catalyzed coupling of boronic acids with N-thio(alkyl, aryl, heteroaryl)imides.
[reaction: see text] A new synthesis of thioethers is described. The reaction of boronic acids with aryl, heteroaryl, and alkyl N-thioimides in the presence of catalytic quantities of a Cu(I) carboxylate affords good to excellent yields of thioethers. This reaction takes place in the absence of a base under mild conditions (THF, 45-50 degrees C, 2.5-12 h) and represents an interesting complement to known methods for thioether synthesis.
Savarin
Cecile
C
Emory University, Department of Chemistry, 1515 Pierce Drive, Atlanta, Georgia 30322, USA.
Srogl
Jiri
J
Liebeskind
Lanny S
LS
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D015394:Molecular Structure; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D001897:Boronic Acids; D004220:Disulfides; D007094:Imides; D013440:Sulfides; D003300:Copper