Iridium complexes of CCC-pincer N-heterocyclic carbene ligands: Synthesis and catalytic C-H functionalization

Anthony R. Chianese, Allen Mo, Nicole L. Lampland, Raymond L. Swartz, Paul T. Bremer

Research output: Contribution to journalArticlepeer-review

127 Scopus citations

Abstract

A series of four meta-phenylene-bridged bis-benzimidazolium chlorides were synthesized as precursors to rigid, monoanionic, CCC-pincer N-heterocyclic carbene ligands. For ligands with mesityl, 3,5-xylyl, or 3,5-di-tert-butylphenyl side groups, reaction with [Ir(1,5-cyclooctadiene)Cl]2 in acetonitrile with either excess triethylamine or stoichiometric cesium fluoride as base gave neutral, iridium(III) pincer complexes of the formula Ir(CCC)HCl(MeCN), which were purified by chromatography on silica gel. Metalation failed under these conditions for a 2,6-diisopropylphenyl-substituted derivative. In combination with NaOtBu, these complexes form active catalysts for the acceptorless dehydrogenation of cyclooctane and for arene C-H borylation in neat arene solvent.

Original languageEnglish
Pages (from-to)3019-3026
Number of pages8
JournalOrganometallics
Volume29
Issue number13
DOIs
StatePublished - Jul 12 2010

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