Issue 9, 2021

Pd/LA-catalyzed decarboxylation enabled exclusive [5 + 2] annulation toward N-aryl azepanes and DFT insights

Abstract

A practical and straightforward methodology towards the synthesis of non-fused N-aryl azepane derivatives with diversity is described. These Pd/LA-catalyzed reactions proceed smoothly under extremely mild conditions with ample reaction scope and CO2 as the byproduct. The resulting products can be easily converted into a range of highly functionalized azepanes. The synthetic value of this protocol is further proved in the formal synthesis of a pharmaceutically relevant Proheptazine derivative. DFT calculations revealed the details of the reaction pathway and the origin of this unusual exclusive [5 + 2] rather than empirical [3 + 2] annulation process.

Graphical abstract: Pd/LA-catalyzed decarboxylation enabled exclusive [5 + 2] annulation toward N-aryl azepanes and DFT insights

Supplementary files

Article information

Article type
Research Article
Submitted
16 яну 2021
Accepted
11 фев 2021
First published
18 фев 2021

Org. Chem. Front., 2021,8, 1902-1909

Pd/LA-catalyzed decarboxylation enabled exclusive [5 + 2] annulation toward N-aryl azepanes and DFT insights

T. Liu, Y. Fang, L. Zuo, Y. Yang, Y. Liu, W. Chen, L. Dang and W. Guo, Org. Chem. Front., 2021, 8, 1902 DOI: 10.1039/D1QO00070E

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