Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate.
Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.
Savarin
C
C
Emory University, Department of Chemistry, 1515 Pierce Drive, Atlanta, Georgia 30322, USA.
Srogl
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J
Liebeskind
L S
LS
D000478:Alkylation; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D001897:Boronic Acids; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; C415665:palladium thiolate