Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids.
A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields.
Zhang
Zhihui
Z
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Liebeskind
Lanny S
LS
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013861:Thiocyanates / Q000737:chemistry*
D001897:Boronic Acids; D003486:Cyanides; D013861:Thiocyanates; D010165:Palladium; D003300:Copper; C034658:benzyl thiocyanate