National Research Institute of Chinese Medicine, Ministry of Health and Welfare , Taipei 11221, Taiwan, Republic of China.
J Org Chem. 2017 Oct 20;82(20):10855-10865. doi: 10.1021/acs.joc.7b01626. Epub 2017 Oct 2.
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.
开发了一种两步法高效合成 3-(2-烯烃苄基)-4H-色烯-4-酮的策略。第一步是（E）-3-（二甲基氨基）-1-（2-羟基苯基）-2-丙烯-1-酮与溴化苄之间的环化苄基化反应，生成同型异黄酮。第二步涉及分子间 Pd 催化的π-螯合辅助 C-H 键烯烃化反应。利用色酮的 C-2/C-3 双键，钯催化的芳基 C-H 键活化可以官能化生成中等到高产率的邻位烯烃化衍生物。
