Multi-step reaction with 10 steps
1.1: indium iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 17 h / 20 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13.58 h / 0 - 20 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / Molecular sieve; Inert atmosphere
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.83 h / -78 - 20 °C / Inert atmosphere
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.58 h / -78 - -40 °C / Inert atmosphere
5.2: -40 - 20 °C / Inert atmosphere
6.1: boron trifluoride diethyl etherate / toluene / 0.5 h / -78 °C / Inert atmosphere
7.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 20 °C / Inert atmosphere
8.1: Schwartz's reagent / benzene / Inert atmosphere; Heating
8.2: -25 °C / Inert atmosphere
9.1: chromium dichloride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 20 °C / Inert atmosphere
10.1: dmap; triethylamine / dichloromethane / 24 h / 30 °C / Inert atmosphere
With
chromium dichloride; dmap; Schwartz's reagent; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; oxalyl dichloride; (R)-N-(2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-6-methylphenyl)methanesulfonamide; indium iodide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene; acetonitrile; benzene;
1.1: Marshall reaction / 5.1: Swarts reaction / 9.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1002/anie.201106762