Natalia Cabrera-Lobera1, M Teresa Quirós1, William W Brennessel2, Michael L Neidig2, Elena Buñuel1, Diego J Cárdenas1. 1. 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. 2. Department of Chemistry , University of Rochester , Rochester , New York 14627 , United States.
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.
We report a Ni-catalyzed diborylative cyclization of n class="Chemical">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.
Authors: Ziyong Wang; Jason Wu; Walid Lamine; Bo Li; Jean-Marc Sotiropoulos; Anna Chrostowska; Karinne Miqueu; Shih-Yuan Liu Journal: Angew Chem Int Ed Engl Date: 2021-08-31 Impact factor: 16.823