Copper(I)-α-ketocarboxylate complexes: Characterization and O 2 reactions that yield copper-oxygen intermediates capable of hydroxylating arenes

Sungjun Hong, Stefan M. Huber, Laura Gagliardi, Christopher C. Cramer, William B. Tolman

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

Abstract

A series of copper(I)-α-ketocarboxylate complexes have been prepared and shown to exhibit variable coordination modes of the α-ketocarboxylate ligand. Reaction with O2 induces decarboxylation of this ligand, and the derived copper-oxygen intermediate(s) has been intercepted, resulting in hydroxylation of an arene substituent on the supporting N-donor ligand. Theoretical calculations have provided intriguing mechanistic notions for the process, notably implicating hydroxylation pathways that involve novel [CuI-OOC(O)R] and [CuII-O-• ↔ CuIII=O2-]+ species.

Original languageEnglish (US)
Pages (from-to)14190-14192
Number of pages3
JournalJournal of the American Chemical Society
Volume129
Issue number46
DOIs
StatePublished - Nov 21 2007

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