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Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Ethers

[Image: see text] An improved method for the nickel-catalyzed Suzuki–Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously substituted styrene derivative...

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Detalles Bibliográficos
Autores principales: Ho, Guo-Ming, Sommer, Heiko, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7025807/
https://www.ncbi.nlm.nih.gov/pubmed/30942604
http://dx.doi.org/10.1021/acs.orglett.9b00946
Descripción
Sumario:[Image: see text] An improved method for the nickel-catalyzed Suzuki–Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously substituted styrene derivatives. An olefinic mixture with respect to the alkenyl ethers can be employed, thereby circumventing the stereodefined synthesis of starting materials. Preliminary mechanistic investigations indicate a nickel-catalyzed olefin isomerization following initial stereoretentive cross-coupling.