Issue 4, 2009

Application of UV-Visspectroscopy to high throughput screening of hydroamination catalysts

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

Article information

Article type
Paper
Submitted
13 Nov 2008
Accepted
24 Dec 2008
First published
23 Jan 2009

New J. Chem., 2009,33, 818-824

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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