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Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Naphthyl and Quinolyl Alcohols with Boronic Acids

Author:
Akkarasamiyo, Sunisa, Margalef, Jèssica, Samec, Joseph S. M.
Source:
Organic letters 2019 v.21 no.12 pp. 4782-4787
ISSN:
1523-7052
Subject:
Suzuki reaction, alcohols, aromatic compounds, boronic acids, chlorides, heterocyclic compounds, moieties, nickel, nuclear magnetic resonance spectroscopy
Abstract:
A nickel-catalyzed C(sp³)–C(sp²) Suzuki cross-coupling of arylboronic acids and (hetero)naphthyl alcohols has been developed. A Ni(dppp)Cl₂ 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.
Agid:
6478219