Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes

Yansong J. Lu, Xiawei Zhang, Santanu Malakar, Karsten Krogh-Jespersen, Faraj Hasanayn, Alan S. Goldman

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9 Scopus citations


Di-isopropylphosphino-substituted pincer-ligated iridium catalysts are found to be significantly more effective for the dehydrogenation of simple tertiary amines to give enamines than the previously reported di-t-butylphosphino-substituted species. It is also found that the di-isopropylphosphino-substituted complexes catalyze dehydrogenation of several β-functionalized tertiary amines to give the corresponding 1,2-difunctionalized olefins. The di-t-butylphosphino-substituted species are ineffective for such substrates; presumably, the marked difference is attributable to the lesser crowding of the di-isopropylphosphino-substituted catalysts. Experimentally determined kinetic isotope effects in conjunction with DFT-based analysis support a dehydrogenation mechanism involving initial pre-equilibrium oxidative addition of the amine α-C-H bond followed by rate-determining elimination of the β-C-H bond.

Original languageEnglish (US)
Pages (from-to)3020-3028
Number of pages9
JournalJournal of Organic Chemistry
Issue number5
StatePublished - Mar 6 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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