Copper-Mediated Chelation-Assisted Ortho Nitration of (Hetero)arenes
Department of Chemistry, Northeast Normal University, Changchun 130024, China, and State Key Laboratory of Fine Chemicals, School of Chemical Engineering, University of Technology, Dalian 116012, China
Org. Lett., 2011, 13 (24), pp 6536–6539
DOI: 10.1021/ol2028288
Publication Date (Web): November 11, 2011
Copyright © 2011 American Chemical Society
Abstract
A novel copper-mediated chelation-assisted ortho C–H nitration of (hetero)arenes has been developed for the first time, which used dioxygen as terminal oxidant and 1,2,3-TCP as solvent, leading to the synthesis of nitroaromatics with excellent regioselectivity and in good yields. Mechanistic investigations indicate a mechanism involving a four-centered transition state, with simultaneous cleavage of an ortho C–H bond and a N–O bond of the nitrate anion on the 2-arylpyridine-coordinated copper(II) complex.
Supporting Information
Experimental procedures, spectra, and analytical data for 2a/2b. This material is available free of charge via the Internet at http://pubs.acs.org.
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