Multi-step reaction with 10 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
1.2: 6 h / 0 °C
2.1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere
3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 25 °C
4.1: tetrahydrofuran / 0 - 25 °C / Inert atmosphere; Molecular sieve
5.1: pyridinium chlorochromate / dichloromethane / 4 h / 25 °C / Inert atmosphere; Molecular sieve
6.1: 2,6-di-tert-butyl-pyridine / nitromethane / 2 h / -20 °C / Inert atmosphere; Molecular sieve
7.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride / N,N-dimethyl-formamide / 16 h / 45 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 0 - 25 °C / Inert atmosphere
9.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 2 h / 25 °C / Inert atmosphere
9.2: 16 h / 20 °C / Inert atmosphere
10.1: ammonium fluoride / methanol / 1 h / 25 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ammonium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-pyridine; sodium hydride; cesium fluoride; 1,1'-carbonyldiimidazole; pyridinium chlorochromate; trifluoroacetic acid;
In
tetrahydrofuran; methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide;
6.1: Friedel Crafts acylation / 7.1: Stille coupling;
DOI:10.1021/ja301326k