Issue 14, 2024

Four-component regio-divergent carbonylative condensations for the sustainable syntheses of acylhydrazones

Abstract

Catalytic carbonylation, which converts multiple green or sustainable starting materials to critical compounds with high atom-economy and chemoselectivity, is a highly desirable and elusive process. Furthermore, carbonylations of alkenes with hydrazines are performed to produce acylhydrazones, which are versatile building blocks for the formation of numerous pharmaceuticals. However, the syntheses of functionalized acylhydrazones involve multi-step reactions that require harsh conditions. Therefore, we herein report practical one-pot catalytic hydrohydrazono-carbonylation condensations of alkenes with hydrazines and aldehydes to form acylhydrazones, with water as the sole coproduct, overcoming the challenge of regioselectivity in multicomponent reactions. Using appropriate ligands, branched or linear N-alkyl-substituted acylhydrazones may be obtained in good-to-high yields with excellent regioselectivities. All the acylhydrazone derivatives are unknown compounds and gram-scale (255.8 g) acylhydrazones are prepared using this protocol, and a possible reaction mechanism is proposed based on control experiments and labeling studies.

Graphical abstract: Four-component regio-divergent carbonylative condensations for the sustainable syntheses of acylhydrazones

Supplementary files

Article information

Article type
Research Article
Submitted
10 Apr 2024
Accepted
27 May 2024
First published
29 May 2024

Org. Chem. Front., 2024,11, 3833-3841

Four-component regio-divergent carbonylative condensations for the sustainable syntheses of acylhydrazones

W. Jiang, M. Pang, Y. Cai, G. Zhang, Y. Liu and G. Zhang, Org. Chem. Front., 2024, 11, 3833 DOI: 10.1039/D4QO00651H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements