Visible-Light Promoted Intramolecular para-Cycloadditions on Simple Aromatics

被引：32

作者：

Chiminelli, Maurizio ^{[1
]}

Serafino, Andrea ^{[1
]}

Ruggeri, Davide ^{[1
]}

Marchio, Luciano ^{[1
]}

Bigi, Franca ^{[1
,2
]}

Maggi, Raimondo ^{[1
]}

Malacria, Max ^{[3
]}

Maestri, Giovanni ^{[1
]}

机构：

[1] Univ Parma, Dept Chem Life Sci & Environm Sustainabil, Parco Area Sci 17-A, I-43124 Parma, Italy

[2] CNR, IMEM, Parco Area Sci 37-A, I-43124 Parma, Italy

[3] Sorbonne Univ, IPCM UMR CNRS 8232, 4 Pl Jussieu, F-75252 Paris, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 12期

关键词：

Allenes; Cycloaddition; Density-Functional Calculations; Energy Transfer; pi Interactions; DIELS-ALDER REACTION; PHOTOCATALYSIS;

D O I：

10.1002/anie.202216817

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dearomative cycloadditions are a powerful tool to access a large chemical space exploiting simple and ubiquitous building blocks. The energetic burden due to the loss of aromaticity has however greatly limited their synthetic potential. We devised a general intramolecular method that overcomes these limitations thanks to the photosensitization of allenamides. The visible-light-promoted process gives complex [2.2.2]-(hetero)-bicyclooctadienes at room temperature, likely through the stabilization of transient (bi)radicals by naphthalene. The reaction tolerates several valuable functionalities, offering a convenient handle for a myriad of applications, including original isoindoles and metal complexes.

引用

页数：6

共 45 条

[31] The effect of π-π stacking interaction of the indole ring with the coordinated phenoxyl radical in a nickel (II)-salen type complex. Comparison with the corresponding Cu(II) complex [J].