Synthesis of Benzoaryl-5-yl(2-hydroxyphenyl)methanones via Photoinduced Rearrangement of (E)-3-Arylvinyl-4H-chromen-4-ones

被引：42

作者：

Fang, Jinming

Wang, Tao

Li, Chenchen

Wang, Rui

Lei, Xiaoyu

Liang, Yong ^{[2
]}

Zhang, Zunting ^{[1
]}

机构：

[1] Shaanxi Normal Univ, Natl Engn Lab Resource Dev Endangered Crude Drugs, Key Lab, Minist Educ Med Resources & Nat Pharmaceut Chem, Xian 710119, Shaanxi, Peoples R China

[2] Beckman Res Inst City Hope, Dept Mol Med, Duarte, CA 91010 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 21期

基金：

中国国家自然科学基金;

关键词：

H BOND FUNCTIONALIZATION; C-O ADDITION; PHOTOCHEMICAL-REACTIONS; SELECTIVE INHIBITORS; CARBOXYLIC-ACIDS; DIARYLETHENES; HETEROARENES; DERIVATIVES; CATALYSIS; TRIFLUOROMETHYLATION;

D O I：

10.1021/acs.orglett.7b03007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoary1-5-y1-(2-hydroxyphenyl)methanones were obtained in 77-95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of alpha,alpha ' diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.

引用

页码：5984 / 5987

页数：4

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