Issue 15, 2021

Mechanical bonding activation in rotaxane-based organocatalysts

Abstract

We report herein the enhanced efficiency as organocatalysts of a series of succinamide-based hydrogen-bonded [2]rotaxanes functionalized with an acyclic secondary amine as the catalytically active site. We also evaluated their catalytic activity, compareds with that of their non-interlocked threads, in an iminium-type process between crotonaldehyde and acetylacetone. The presence of an interlocked polyamide macrocycle notably increased the catalytic activity of the entwined organocatalysts. The mechanized catalysts rapidly form a reactive iminium intermediate with the aldehyde, increasing its population. The hydrogen-bonding interaction established between the macrocycle and the electrophile has been proposed as one of the reasons for the rapid formation and stabilization of this key intermediate.

Graphical abstract: Mechanical bonding activation in rotaxane-based organocatalysts

Supplementary files

Article information

Article type
Research Article
Submitted
21 май 2021
Accepted
27 май 2021
First published
01 июн 2021

Org. Chem. Front., 2021,8, 4202-4210

Mechanical bonding activation in rotaxane-based organocatalysts

J. D. M. Perez, J. Puigcerver, T. Orlando, A. Pastor, M. A. P. Martins, M. Alajarin, A. Martinez-Cuezva and J. Berna, Org. Chem. Front., 2021, 8, 4202 DOI: 10.1039/D1QO00789K

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