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Issue 4, 2009
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Application of UV-Vis spectroscopy to high throughput screening of hydroamination catalysts

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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.

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

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Publication details

The article was received on 13 Nov 2008, accepted on 24 Dec 2008 and first published on 23 Jan 2009


Article type: Paper
DOI: 10.1039/B820357C
New J. Chem., 2009,33, 818-824

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

    D. F. Kennedy, B. A. Messerle and S. L. Rumble, New J. Chem., 2009, 33, 818
    DOI: 10.1039/B820357C

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