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Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron

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Abstract

A highly chemo- and stereoselective nickel-catalyzed borylative cyclization of 1,6-enynes with bis(pinacolato)diboron is described. Enynes containing an electron-deficient alkene such as a vinyl ketone provided alkenylboronates while enynes containing a terminal alkene gave homoallylic boronates. A plausible mechanism involving a nickelacyclopentene intermediate is proposed. In addition, the resulted alkenyl- or homoallylic boronates can be transformed to the corresponding ketones and alcohols via oxidation. Application to a palladium-catalyzed cross coupling reaction of alkenylboronates with aromatic halides has been demonstrated as well.

Graphical abstract: Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron

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Publication details

The article was received on 26 Apr 2017, accepted on 15 May 2017 and first published on 17 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00321H
Citation: Org. Chem. Front., 2017, Advance Article
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    Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron

    J. Hsieh, Y. Hong, C. Yang, S. Mannathan and C. Cheng, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00321H

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