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Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Naphthyl and Quinolyl Alcohols with Boronic Acids
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0001-8735-5397
Rekke forfattare: 32019 (engelsk)Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, nr 12, s. 4782-4787Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. Vol. 21, nr 12, s. 4782-4787
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URN: urn:nbn:se:su:diva-171103DOI: 10.1021/acs.orglett.9b01669ISI: 000473116000082PubMedID: 31184197OAI: oai:DiVA.org:su-171103DiVA, id: diva2:1342784
Tilgjengelig fra: 2019-08-14 Laget: 2019-08-14 Sist oppdatert: 2019-08-14bibliografisk kontrollert

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Akkarasamiyo, SunisaMargalef, JèssicaSamec, Joseph S. M.
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