Palladium(0)-Catalyzed Alkylative Cyclization of Alkynals and Alkynones: Remarkable trans-Addition of Organoboronic Reagents
- 11 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (5), 1406-1407
- https://doi.org/10.1021/ja056458o
Abstract
Palladium/monophosphine complexes catalyze trans-selective arylative, alkenylative, and alkylative cyclization reactions of alkynals and alkynones with organoboronic reagents. These reactions afford six-membered allylic alcohols with endo-tri- or tetrasubstituted olefin groups and/or five-membered counterparts with exo olefin groups. The ratios of these products are dramatically affected by alkyne substituents as well as the phosphine ligand. The remarkable trans-selectivity of the process results from the novel reaction mechanism involving oxidative addition without oxametallacycle formation.Keywords
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