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Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki-Heck Reaction. | LitMetric

Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki-Heck Reaction.

Org Lett

Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada.

Published: September 2024

We report a palladium-catalyzed synthesis of α-vinyl boronates via a regioselective Mizoroki-Heck reaction between aryl triflates and vinyl boronates. This selectivity is achieved by the use of a 1,5-diaza-3,7-diphosphacyclooctane (PN) ligand, which results in minimal formation of the more commonly observed (linear) β-product. The choice of base, solvent, and presence of water are shown to be critical for controlling this outcome, with organic bases, nonpolar solvents, and anhydrous conditions favoring the Heck product and suppressing the competitive Suzuki-Miyaura coupling product.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c02866DOI Listing

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