Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights

Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford

doi:10.1021/ja051402f

Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights

J Am Chem Soc. 2005 May 25;127(20):7330-1. doi: 10.1021/ja051402f.

Authors

Dipannita Kalyani¹, Nicholas R Deprez, Lopa V Desai, Melanie S Sanford

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, 48109-1055, USA.

PMID: 15898779
DOI: 10.1021/ja051402f

Abstract

This paper describes a new palladium-catalyzed method for C-H activation/carbon-carbon bond formation with hypervalent iodine arylating agents. This transformation has been applied to a variety of arene and benzylic substrates containing different directing groups (pyridines, quinolines, oxazolidinones, and amides) and proceeds with high levels of regiocontrol. Mechanistic experiments provide preliminary evidence in support of an unusual mechanism for this transformation involving a Pd(II)/Pd(IV) catalytic cycle.