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Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates. | LitMetric

Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates.

Org Lett

Departamento de Química Orgánica , Facultad de Ciencias, Universidad Autónoma de Madrid, Institute for Advanced Research in Chemical Sciences (IAdChem), Av. Francisco Tomás y Valiente 7, Cantoblanco 28049 , Madrid , Spain.

Published: August 2019

AI Article Synopsis

  • - The study presents a nickel-catalyzed process that allows the creation of carbocycles and heterocycles from enynes, producing alkyl- and alkenylboronates efficiently.
  • - This reaction is environmentally friendly due to its full atom-economy and uses a cost-effective nickel catalyst, making it accessible for various applications.
  • - The research uncovers a unique mechanism involving the activation of enynes by nickel and identifies a rare dinuclear nickel(I) complex as an intermediate in the reaction.

Article Abstract

We report a Ni-catalyzed diborylative cyclization of enynes that affords carbo- and heterocycles containing both alkyl- and alkenylboronates. The reaction is fully atom-economical, shows a broad scope, and employs a powerful and inexpensive catalytic Ni-based system. The reaction mechanism seems to involve activation of the enyne by Ni(0) through oxidative cyclometalation of the enyne prior to diboron reagent activation. An unprecedented dinuclear bis(organometallic) Ni(I) intermediate complex was isolated.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7196956PMC
http://dx.doi.org/10.1021/acs.orglett.9b02485DOI Listing

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