Issue 36, 2020
From the journal:

Chemical Communications

Photochemical α-carboxyalkylation of tryptophols and tryptamines via C–H functionalization†

Zhiqiang Pan,‡a   Yuchang Liu,‡a   Fengchi Hu,a   Qinglong Liu,a   Wenbin Shanga  and  Chengfeng Xia ORCID logo *a  

* Corresponding authors

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

Abstract

A process for the α-carboxyalkylation of tryptophols and tryptamines by the functionalization of C–H bonds under visible light irradiation has been developed. The photochemical strategy activated the C–Br bonds of α-bromo-alkylcarboxylic esters to provide carbon-centered radicals under the catalysis of Ir(III) photocatalyst and coupled with indole derivatives. This methodology displayed wide functional group tolerance and excellent regioselectivity, and was applied to the late-stage functionalization and preparation of indole-containing hybrids.

Graphical abstract: Photochemical α-carboxyalkylation of tryptophols and tryptamines via C–H functionalization

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Article information

DOI
https://doi.org/10.1039/D0CC00847H
Article type
Communication
Submitted
02 Feb 2020
Accepted
18 Mar 2020
First published
19 Mar 2020

Chem. Commun., 2020,56, 4930-4933

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Photochemical α-carboxyalkylation of tryptophols and tryptamines via C–H functionalization

Z. Pan, Y. Liu, F. Hu, Q. Liu, W. Shang and C. Xia, Chem. Commun., 2020, 56, 4930 DOI: 10.1039/D0CC00847H

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