Issue 13, 2024

Entropy effects in temperature-regulated nickel-catalyzed regiodivergent alkene hydroalkylation

Abstract

Temperature-regulated nickel-catalyzed regiodivergent alkene hydroalkylation has been reported, yet there is a lack of a reasonable explanation for the regulation mechanism. Herein, we conduct a systematic analysis of the pertinent data, aiming to reveal the potential role and mechanism of temperature in regioselectivity. Alkyl radicals trapped by Ni(I) species are reasonably well-formed. Following this, entropic effects at different temperatures are found to be responsible for the regioselectivity turnover. Intramolecular transformation (β-H elimination) was less sensitive than the intermolecular step (radical addition and reductive elimination) for the entropy change; influencing the entropy response through temperature led to the regioselectivity regulation. These findings deepen our understanding of the influence of temperature on the regioselectivity of nickel-catalyzed alkene hydroalkylation.

Graphical abstract: Entropy effects in temperature-regulated nickel-catalyzed regiodivergent alkene hydroalkylation

Supplementary files

Article information

Article type
Research Article
Submitted
15 Mar 2024
Accepted
14 May 2024
First published
14 May 2024

Org. Chem. Front., 2024,11, 3648-3654

Entropy effects in temperature-regulated nickel-catalyzed regiodivergent alkene hydroalkylation

D. Liu, J. Wang, X. Lu and Y. Fu, Org. Chem. Front., 2024, 11, 3648 DOI: 10.1039/D4QO00486H

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