1: With hydrogen; [rhodium(I)(carbonyl)2(acetylacetonate)] in tetrahydrofuran T=100°C; Fischer indolization; 72 h; pressure; 2: With sulfuric acid in tetrahydrofuran Wagner-Meerwein rearrangement; 3 h; Heating;

1.1: H2SO4; NaNO2 / H2O / 0 °C 1.2: 60 percent / NaI / H2O / 0.25 h / 20 °C 2.1: 56 percent / Cs2CO3; CuI; phenanthroline / dimethylformamide / 72 h / 80 °C 3.1: H2 / Rh(acac)(CO)2 / tetrahydrofuran / 72 h / 100 °C / pressure 3.2: 44 percent / H2SO4 / tetrahydrofuran / 3 h / Heating View Scheme

[(η5-C5Me5)2Rh2(μ-Cl)2Cl2]; sodium acetate; acetic acid; pentan-3-one in ethanol T=110°C; 20 h; Sealed tubeInert atmosphere; regioselective reaction;

silver hexafluoroantimonate; [{(η5-C5Me5)RhCl}2(μ-Cl)2]; copper (II) acetate monohydrate in methanol T=90°C; Schlenk techniqueInert atmosphere; regioselective reaction;

1.1: 56 percent / Cs2CO3; CuI; phenanthroline / dimethylformamide / 72 h / 80 °C 2.1: H2 / Rh(acac)(CO)2 / tetrahydrofuran / 72 h / 100 °C / pressure 2.2: 44 percent / H2SO4 / tetrahydrofuran / 3 h / Heating View Scheme

T=250°C; Fischer indole synthesis; 0.0166667 h;