3 years ago

Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation and Catalytic C–H Bond Functionalization Using Palladium(II)

Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation and Catalytic C–H Bond Functionalization Using Palladium(II)
Chi Fong, Kuei-Chien Tang, Yu-Feng Lin, Wen-Tai Li, Wan-Ling Peng, Yi-En Liang
An efficient strategy for synthesizing 3-(2-olefinbenzyl)-4H-chromen-4-one in two steps was developed. The first step is a cyclobenzylation reaction between (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one and benzyl bromide to produce homoisoflavonoid. The second step involves intermolecular Pd-catalyzed π-chelating-assisted C–H bond olefination. Using the C-2/C-3 double bond of chromone, palladium-catalyzed aryl C–H bond activation can be functionalized to generate ortho-olefination derivatives in moderate to high yields.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01626

DOI: 10.1021/acs.joc.7b01626

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