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

Chemical Science 2018 Februrary 8
In the presence of 5 mol% Pd(OAc)2 , 1 equiv. of norbornene, and K2 CO3 , 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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