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J Am Chem Soc. 2006 May 31;128(21):6790-1.

Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant.

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1
Department of Chemistry MS015, Brandeis University, Waltham, MA 02454-9110, USA.

Abstract

Cu(II)-catalyzed acetoxylation and halogenation of aryl C-H bonds are developed. ortho-Selectivity was observed with a wide range of 2-arylpyridine substrates. Both mono- and difunctionalizations are achieved by tuning the reaction conditions. Excellent functional group tolerance and use of O2 as a stoichiometric oxidant are significant advantages over our recently developed Pd-catalyzed C-H functionalization reactions. These newly discovered reaction conditions are also applicable for cyanation, amination, etherification, and thioetherification of aryl C-H bonds. Mechanistic investigations are carried out to gain insights into the Cu(II)-catalyzed C-H functionalization reactions.

PMID:
16719450
DOI:
10.1021/ja061715q
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