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The vinylogous Catellani reaction: A combined computational and experimental study

Abstract

In the presence of 5 mol % Pd(OAc)2, 1 equiv of norbornene, and K2CO3, the reaction of 4-iodo-2-quinolones with tertiary benzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving the vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.

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Publication details

The article was received on 30 Sep 2017, accepted on 29 Nov 2017 and first published on 30 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC04265E
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
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    The vinylogous Catellani reaction: A combined computational and experimental study

    Y. Yamamoto, T. Murayama, J. Jiang, T. Yasui and M. Shibuya, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC04265E

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