TY - JOUR
T1 - Application of UV-Vis spectroscopy to high throughput screening of hydroamination catalysts
AU - Kennedy, Danielle F.
AU - Messerle, Barbara A.
AU - Rumble, Sarah L.
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=64549131720&partnerID=8YFLogxK
U2 - 10.1039/b820357c
DO - 10.1039/b820357c
M3 - Article
AN - SCOPUS:64549131720
SN - 1144-0546
VL - 33
SP - 818
EP - 824
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 4
ER -