Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed C­C bond-forming reactions

Batey, Robert A.; Quach, Tan D.; Shen, Ming; Thadani, Avinash N.; Smil, David V.; Li, Sze-Wan; MacKay, D. Bruce

doi:10.1351/pac200274010043

Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 43-55

http://dx.doi.org/10.1351/pac200274010043

Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed CC bond-forming reactions

Robert A. Batey, Tan D. Quach, Ming Shen, Avinash N. Thadani, David V. Smil, Sze-Wan Li and D. Bruce MacKay

Department of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, M5S 3H6, Canada

Abstract: The use of air- and water-stable organoboron compounds for CC bond-forming reactions are reported. These studies include the Lewis acid-promoted additions of boronic esters to N-acyliminium ions and allyl and crotyltrifluoroborate salts to aldehydes. Aryl and alkenyltrifluoroborate salts will add to aldehydes under the influence of rhodium catalysis or in the presence of zinc metal. These salts also participate in palladium-catalyzed SuzukiMiyaura and other cross-coupling reactions. Finally, a new type of N-heterocyclic carbene ligand is reported and used for Pd-catalyzed SuzukiMiyaura couplings.