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 oct. 2022
Accepted
25 nov. 2022
First published
25 nov. 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

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