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

ABSTRACT: 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.

SUBMITTER: Ho GM

PROVIDER: S-EPMC7025807 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Ho Guo-Ming GM Sommer Heiko H Marek Ilan I

Organic letters 20190403 8

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 ole ...[more]

PMID: 30942604

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