Jump to main content
Jump to site search


t-BuONa-mediated direct C–H halogenation of electron-deficient (hetero)arenes

Author affiliations

Abstract

An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl–Caryl cross-coupling reaction.

Graphical abstract: t-BuONa-mediated direct C–H halogenation of electron-deficient (hetero)arenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 Dec 2017, accepted on 10 Jan 2018 and first published on 10 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03081A
Citation: Org. Biomol. Chem., 2018, Advance Article
  •   Request permissions

    t-BuONa-mediated direct C–H halogenation of electron-deficient (hetero)arenes

    X. Liu, X. Zhao, F. Liang and B. Ren, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB03081A

Search articles by author

Spotlight

Advertisements