1.1: N-ethyl-N,N-diisopropylamine; hydrogen; Rh(acetylacetonate)(CO)2; C75H54N4O8P2 / dichloromethane / 24 h / 20 °C / 15001.5 Torr / |Inert atmosphere; |Schlenk technique 2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 0.17 h / |Inert atmosphere; |Schlenk technique 2.2: |Inert atmosphere; |Schlenk technique 3.1: ethanol / 0.75 h / 20 °C / |Schlenk technique 3.2: 0.75 h / 0 - 20 °C 4.1: trimethylaluminum / tetrahydrofuran; n-heptane / 48 h / 0 - 70 °C / |Schlenk technique View Scheme

1: 60 percent / TiCl4 / benzene / 1 h / 0 - 5 °C 2: 25 percent / ethanol / 24 h / Irradiation View Scheme

1.1: ethanol / 0.75 h / 20 °C / |Schlenk technique 1.2: 0.75 h / 0 - 20 °C 2.1: trimethylaluminum / tetrahydrofuran; n-heptane / 48 h / 0 - 70 °C / |Schlenk technique View Scheme

1.1: hydrogen; Rh(acetylacetonate)(CO)2; C75H54N4O8P2 / dichloromethane / 25 h / 30 °C / 15001.5 Torr / |Inert atmosphere; |Autoclave 2.1: ethanol / 0.75 h / 20 °C / |Schlenk technique 2.2: 0.75 h / 0 - 20 °C 3.1: trimethylaluminum / tetrahydrofuran; n-heptane / 48 h / 0 - 70 °C / |Schlenk technique View Scheme

in ethanol 24 h; Irradiation;

in ethanol Irradiation;

in ethanol Irradiation; Yield given. Yields of byproduct given;

1: 2-(3-oxopropane)benzoic acid With potassium hydrogencarbonate; methyl iodide Inert atmosphereSchlenk technique; 2: N-butylamine With sodium tetrahydroborate Inert atmosphereSchlenk technique; 3: With trimethylaluminum Inert atmosphereSchlenk technique;

in ethanol 24 h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;