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

Org Lett

Department of Organic Chemistry-I, University of the Basque Country (UPV-EHU) , Joxe Mari Korta R&D Center, Av Tolosa 72, 20018 Donostia-San Sebastián, Spain.

Published: February 2017

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.

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http://dx.doi.org/10.1021/acs.orglett.7b00275DOI Listing

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