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Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Naphthyl and Quinolyl Alcohols with Boronic Acids
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8735-5397
Number of Authors: 32019 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, no 12, p. 4782-4787Article in journal (Refereed) Published
Abstract [en]

A nickel-catalyzed C(sp(3))-C(sp(2)) Suzuki cross-coupling of arylboronic acids and (hetero)naphthyl alcohols has been developed. A Ni(dppp) Cl-2 complex showed the highest efficiency and broadest substrate scope. High functional group tolerance has been achieved where 35 compounds could be generated in good to excellent yields, including both primary and secondary benzylic alcohols. Mechanistic studies using multiple NMR techniques as well as ESI-HRMS showed that the C-O cleavage is facilitated by an activation of the benzylic alcohol through formation of a boronic ester intermediate.

Place, publisher, year, edition, pages
2019. Vol. 21, no 12, p. 4782-4787
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Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-171103DOI: 10.1021/acs.orglett.9b01669ISI: 000473116000082PubMedID: 31184197OAI: oai:DiVA.org:su-171103DiVA, id: diva2:1342784
Available from: 2019-08-14 Created: 2019-08-14 Last updated: 2019-08-14Bibliographically approved

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Akkarasamiyo, SunisaMargalef, JèssicaSamec, Joseph S. M.
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