Issue 17, 2024
From the journal:

Organic & Biomolecular Chemistry

Dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones†

Kai-Cheng Yang,a   Shi-Lu Zheng,a   Zhong Wen,a   Yu-Shan Zhang,a   Hai-Liang Nib  and  Long Chen ORCID logo *a  

* Corresponding authors

a Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, 2025 Chengluo Avenue, Chengdu 610016, P. R. China
E-mail: chenlong@cdu.edu.cn

b College of Chemistry and Materials Science, Sichuan Normal University, 5 Jing An Road, Chengdu 610066, P. R. China

Abstract

A brand-new procedure for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones has been disclosed via a HOTf or Fe(OTf)3-catalyzed dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes. Aryl, alkenyl and alkyl terminal alkynes are suitable to couple with a broad range of 3-hydroxyisoindolinones to afford the desired products in moderate to good yields. This protocol features the use of an inexpensive catalyst, mild reaction conditions, broad substrate scope and easy elaboration of the products.

Graphical abstract: Dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones

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Article information

DOI
https://doi.org/10.1039/D4OB00190G
Article type
Paper
Submitted
06 Feb 2024
Accepted
03 Apr 2024
First published
03 Apr 2024

Org. Biomol. Chem., 2024,22, 3453-3458

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Dehydrative alkynylation of 3-hydroxyisoindolinones with terminal alkynes for the synthesis of 3-alkynylated 3,3-disubstituted isoindolinones

K. Yang, S. Zheng, Z. Wen, Y. Zhang, H. Ni and L. Chen, Org. Biomol. Chem., 2024, 22, 3453 DOI: 10.1039/D4OB00190G

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