Regioselective Synthesis of α-Vinyl Boronates via a Pd-Catalyzed Mizoroki–Heck Reaction
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 (P<sub>2</sub>N<sub>2</sub>) 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.
Authors
- Stephen G. Newman (ORCID: https://orcid.org/0000-0003-1949-5069)
- Eric S. Isbrandt (ORCID: https://orcid.org/0009-0004-6916-9151)
- Zichuan Chen
Institutions
- University of Ottawa (CA)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-30
- DOI
- https://doi.org/10.1021/acs.orglett.4c02866
- Citations
- 3
- Primary Topic
- Catalytic Cross-Coupling Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Canada Research Chairs
- Natural Sciences and Engineering Research Council of Canada