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Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates
Natalia Cabrera-Lobera1, M Teresa Quirós1, William W Brennessel2
1Departamento 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.
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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