Selective C(sp)-H Halogenation of "Click" 4-Aryl-1,2,3-triazoles.

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ID: 57904
2017
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Abstract
Selective bromination reactions of "click compounds" are described. Electron-neutral and electron-deficient arenes selectively undergo unprecedented Pd-catalyzed C-H ortho-halogenations assisted by simple triazoles as modular directing groups, whereas electron-rich arenes are regioselectively halogenated following an electrophilic aromatic substitution reaction pathway. These C-H halogenation procedures exhibit a wide group tolerance, complement existing bromination procedures, and represent versatile synthetic tools of utmost importance for the late-stage diversification of "click compounds". The characterization of a triazole-containing palladacycle and density functional theory studies supported the mechanism proposal.
Reference Key
goitia2017selectiveorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Goitia, Asier;Gómez-Bengoa, Enrique;Correa, Arkaitz;
Journal Organic letters
Year 2017
DOI
10.1021/acs.orglett.7b00275
URL
Keywords
Antimicrobial activity Click chemistry molecular docking 1,2,3-triazole-1,2,4-triazole hybrids lipophilic side chain

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