Application of UV-Vis spectroscopy to high throughput screening of hydroamination catalysts

Danielle F. Kennedy, Barbara A. Messerle, Sarah L. Rumble

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Potential catalysts for the hydroamination of 2-(2-phenylethynyl)aniline 2 which have been identified through high throughput screening methods were investigated. Two complexes were shown to be highly active hydroamination catalysts in acetone: the in situ combinations of [Rh(CO)2Cl] 2-mesBIAN-NaBF4 (mesBIAN = bis(2,4,6-trimethylphenylimino) acenapthene) and [Ir(COD)Cl]2-NaBF4 (COD = 1,5-cyclooctadiene). The isolated complexes [M(N-N)XCl]BF4 (M = Rh, Ir; N-N = bidentate nitrogen donor ligand; X = CO or Cp*) were found to be inactive as catalysts for the conversion of 2 to 3. However, chloride abstraction from these complexes through the addition of AgBF4 was found to generate extremely active catalysts. Particularly active was the complex [Rh(CO)ClmesBIAN]-AgBF4 (5 mol%) which achieved complete conversion of 2 to 3 in 12 minutes at 50 °C. Also identified was the formation of the unusual product, N-(2-methylvinyl)-2-phenylindole 5, catalysed by [IrCp*Cl2]2-NaBF4 from starting material 2via the incorporation of one molecule of acetone.

Original languageEnglish
Pages (from-to)818-824
Number of pages7
JournalNew Journal of Chemistry
Volume33
Issue number4
DOIs
Publication statusPublished - 2009
Externally publishedYes

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