Issue 1, 2023

N-Haloimide-enabled halogenation via halogen-bond-assisted C–C activation of alkanols

Abstract

The selective halogenation of the inert C–C bonds of alcohol-based feedstock is of tremendous significance in synthetic chemistry. Previous halogenation usually requires a metal catalyst and/or an oxidant and is limited to the cleavage of the C–C bonds of tertiary cycloalkanols. Herein, we report a broadly applicable strategy for the synthesis of iodoalkanes, bromoalkanes and chloroalkanes via the halogen-bond-assisted C–C activation of cyclic and acyclic alkanols in the absence of catalysts and oxidants, where the inexpensive N-haloimides act as bifunctional reagents to activate and halogenate alcohols. This redox-neutral protocol is a general method for the halogenation of the C–C bonds of primary, secondary, and tertiary alkanols, thus installing three types of halogen atoms and boronic esters through one-pot deiodination–borylation in a wide range of feedstock chemicals in a practical and sustainable fashion.

Graphical abstract: N-Haloimide-enabled halogenation via halogen-bond-assisted C–C activation of alkanols

Supplementary files

Article information

Article type
Paper
Submitted
08 אוק 2022
Accepted
25 נוב 2022
First published
25 נוב 2022

Green Chem., 2023,25, 221-228

N-Haloimide-enabled halogenation via halogen-bond-assisted C–C activation of alkanols

Y. Geng, Y. Ma, R. Huang, X. Li and S. Yu, Green Chem., 2023, 25, 221 DOI: 10.1039/D2GC03768H

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