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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 o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C-H cleavage is proposed based on the results of control experiments and density functional theory calculations.

SUBMITTER: Yamamoto Y

PROVIDER: S-EPMC5885779 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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The vinylogous Catellani reaction: a combined computational and experimental study.

Yamamoto Y Y Murayama T T Jiang J J Yasui T T Shibuya M M

Chemical science 20171130 5

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

PMID: 29675164

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