Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 - 0 °C / Inert atmosphere
4.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere
7.1: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 20 °C / Inert atmosphere
8.1: (1-(4-((triethylammonium chloride)methyl)benzyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)gold(I)chloride / tetrahydrofuran / 2 h
9.1: hydrogen; palladium on activated charcoal / methanol / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / Inert atmosphere
With
1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; palladium on activated charcoal; (1-(4-((triethylammonium chloride)methyl)benzyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)gold(I)chloride; tetrabutyl ammonium fluoride; hydrogen; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/c5ob01286d