Organotrifluoroborates are strong nucleophiles and react with electrophiles without transition-metal catalysts.[6]
Mechanism
The mechanism of organotrifluoroborate-based Suzuki-Miyaura coupling reactions has recently been investigated in detail. The organotrifluoroborate hydrolyses to the corresponding boronic acid in situ, so a boronic acid can be used in place of an organotrifluoroborate, as long as it is added slowly and carefully.[7][8]
^Berionni, G.; Maji, B.; Knochel, P.; Mayr, H. (2012). "Nucleophilicity parameters for designing transition metal-free C–C bond forming reactions of organoboron compounds". Chemical Science. 3 (3): 878–882.
doi:
10.1039/C2SC00883A.
^Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. (2010). "Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride". Angew. Chem. Int. Ed.49 (30): 5156–60.
doi:
10.1002/anie.201001522.
PMID20544767.