Issue 10, 2021
From the journal:

Chemical Communications

Chichibabin pyridinium synthesis via oxidative decarboxylation of photoexcited α-enamine acids†

Zhiqiang Pan,a   Fengchi Hu,a   Di Jiang,a   Yuchang Liua  and  Chengfeng Xia ORCID logo *a  

* Corresponding authors

a Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
E-mail: xiacf@ynu.edu.cn

Abstract

A visible light-induced decarboxylative Chichibabin pyridinium synthesis between α-amino acids and aldehydes was developed. When the in situ generated α-enamine acids were photoexcited, they were oxidized by aerobic oxygen to give radical cation species. After decarboxylation and further oxidation, the generated iminium undergoes Chichibabin cyclization to afford pyridiniums. This photochemical protocol enables the synthesis of various tetra-substituted pyridiniums and related natural products in one-step.

Graphical abstract: Chichibabin pyridinium synthesis via oxidative decarboxylation of photoexcited α-enamine acids

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Article information

DOI
https://doi.org/10.1039/D0CC07636H
Article type
Communication
Submitted
21 Nov 2020
Accepted
22 Dec 2020
First published
23 Dec 2020

Chem. Commun., 2021,57, 1222-1225

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Chichibabin pyridinium synthesis via oxidative decarboxylation of photoexcited α-enamine acids

Z. Pan, F. Hu, D. Jiang, Y. Liu and C. Xia, Chem. Commun., 2021, 57, 1222 DOI: 10.1039/D0CC07636H

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