Nickel-Catalyzed Homo- and Cross-Coupling of Allyl Alcohols via Allyl Boronates

A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B pin with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling o...

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Veröffentlicht in:Organic letters 2020-06, Vol.22 (11), p.4418-4423
Hauptverfasser: Gan, Yi, Hu, Hui, Liu, Yuanhong
Format: Artikel
Sprache:eng
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Zusammenfassung:A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B pin with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01424