General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

被引：142

作者：

Lei, Tao ^{[1
,2
]}

Zhou, Chao ^{[1
,2
]}

Huang, Mao-Yong ^{[1
,2
]}

Zhao, Lei-Min ^{[1
,2
]}

Yang, Bing ^{[1
,2
]}

Ye, Chen ^{[1
,2
]}

Xiao, Hongyan ^{[1
,2
]}

Meng, Qing-Yuan ^{[1
,2
]}

Ramamurthy, Vaidhyanathan ^{[3
]}

Tung, Chen-Ho ^{[1
,2
]}

Wu, Li-Zhu ^{[1
,2
]}

机构：

[1] Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Chinese Acad Sci, Beijing 100190, Peoples R China

[3] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 48期

基金：

中国国家自然科学基金; 美国国家科学基金会;

关键词：

2+2] cycloaddition; chalcones; cinnamic acid; cyclobutanes; visible-light catalysis; CLEAVABLE REDOX AUXILIARIES; SUPRAMOLECULAR PHOTOCHEMISTRY; ENERGY-TRANSFER; CYCLOADDITIONS; PHOTOCYCLOADDITION; PHOTOCATALYSIS; STATE;

D O I：

10.1002/anie.201708559

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host-guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.

引用

页码：15407 / 15410

页数：4

共 36 条

[1] Photochemical Reactions as Key Steps in Natural Product Synthesis [J].