Multi-step reaction with 14 steps
1.1: C52H46O4P2Ru; hydrogen / methanol / 16 h / 37503.8 Torr / Schlenk technique; Sealed tube
2.1: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Schlenk technique; Inert atmosphere
3.1: N-Bromosuccinimide / tetrahydrofuran; water / 5 h / 0 °C / Schlenk technique; Inert atmosphere
3.2: Schlenk technique; Inert atmosphere
4.1: periodic acid / tetrahydrofuran / 1 h / 0 °C
5.1: tetrahydrofuran / 16 h / Schlenk technique; Inert atmosphere; Reflux
6.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / Schlenk technique; Inert atmosphere
7.1: C37H40NOPRh; hydrogen / dichloromethane / 16 h / 0 °C / 37503.8 Torr / Schlenk technique
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - 60 °C / Schlenk technique; Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -30 °C / Schlenk technique; Inert atmosphere
9.2: 16 h / -50 - 20 °C / Schlenk technique; Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Schlenk technique; Inert atmosphere
11.1: triethylamine / dichloromethane / 2 h / 0 °C / Schlenk technique; Inert atmosphere
12.1: sodium hydride / tetrahydrofuran / 0.25 h / Schlenk technique; Inert atmosphere
12.2: 16 h / Schlenk technique; Inert atmosphere
13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / Reflux; Schlenk technique; Inert atmosphere
14.1: hydrogen; platinum on activated charcoal / methanol; dichloromethane / 16 h / Schlenk technique
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; platinum on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; C52H46O4P2Ru; C37H40NOPRh; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; periodic acid; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; water;
8.1: |Swern Oxidation;
DOI:10.1002/anie.202104759