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

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journal contribution
posted on 29.07.2019, 17:04 by Natalia Cabrera-Lobera, M. Teresa Quirós, William W. Brennessel, Michael L. Neidig, Elena Buñuel, Diego J. Cárdenas
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.