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.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
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