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One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki−Miyaura Cross-Coupling

Baumgartner, Yann and Baudoin, Olivier. (2020) One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki−Miyaura Cross-Coupling. ACS Catalysis, 10. pp. 10508-10515.

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Abstract

Chain-walking is a powerful approach toward the functionalization of C–H bonds remote to a functional group. Whereas various Pd-catalyzed migratory cross-couplings have been developed in the past years, the design of an efficient migratory version of the popular Suzuki–Miyaura cross-coupling has remained elusive. The current article reports a one-pot procedure consisting of alkene hydroboration and migratory Suzuki–Miyaura coupling of the resulting alkylboronic acid intermediate. A high regioselectivity for the benzylic position of the initial alkene was achieved by using P(t-Bu)2Me as the ligand and an ortho-substituted aryl electrophile. Regioconvergence from alkene positional and geometrical isomers and long-range migration were demonstrated. Mechanistic investigations indicated that the migration occurs through a partially reversible, nondissociative mechanism.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
e-ISSN:2155-5435
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
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edoc DOI:
Last Modified:08 Sep 2020 11:13
Deposited On:08 Sep 2020 11:12

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