Multi-step reaction with 12 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere
2: dmap / acetonitrile / 0.5 h / 40 °C
3: ammonium acetate / 2 h / 70 °C
4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C
5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
6: triethylamine / dichloromethane / 1 h / 0 - 20 °C
7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8: hydrogenchloride; zinc / methanol; water / 1 h
9: potassium carbonate / acetonitrile / 20 h / 20 °C
10: triethylamine / dichloromethane / 24 h / 20 °C
11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere
12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
With
hydrogenchloride; dmap; sodium tetrahydroborate; silver hexafluoroantimonate; lithium aluminium tetrahydride; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; ammonium acetate; copper diacetate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; zinc;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/acs.orglett.7b01681