Arene-Alkene Cycloaddition

被引:196
作者
Remy, Richard [1 ]
Bochet, Christian G. [1 ]
机构
[1] Univ Fribourg, Dept Chem, Chemin Musee 9, CH-1700 Fribourg, Switzerland
基金
瑞士国家科学基金会;
关键词
INTRAMOLECULAR META-PHOTOCYCLOADDITION; DONOR-ACCEPTOR SYSTEMS; OLEFIN CYCLO-ADDITIONS; CONFORMATIONALLY RESTRAINED 5-PHENYLPENT-1-ENES; PALLADIUM-MEDIATED FRAGMENTATION; CYCLOPROPANE RING FORMATION; DIELS-ALDER ADDITIONS; PHOTOCHEMICAL-REACTIONS; 2-PI+2-PI PHOTOCYCLOADDITION; CHARGE-TRANSFER;
D O I
10.1021/acs.chemrev.6b00005
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of View, both. olefinic and diene;: subunits; however, the Stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are,therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical activation opens interesting perspectives, as one can selectively provide excess. energy to nine of the reactants but not to the product, thus preventing thermal back reaction. Indeed,, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.
引用
收藏
页码:9816 / 9849
页数:34
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