Dichlorination of olefins with trichloroisocyanuric acid (TCCA) and tetrabutylammonium chloride (TBACl)

Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, alpha,beta-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY

Year

2025

Volume

23

Issue

8

Pages

1894-1900

ISSN

1477-0520

eISSN

1477-0539

DOI

10.1039/d4ob01962h

WoS UID

WOS:001395950600001