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The vinylogous Catellani reaction: a combined computational and experimental study
Y Yamamoto1, T Murayama1, J Jiang1
1Department of Basic Medicinal Sciences , Graduate School of Pharmaceutical Sciences , Nagoya University , Chikusa , Nagoya 464-8601 , Japan .
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.
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