Multi-step reaction with 6 steps
1: 1.) Pd2(dba)3, DPPF, t-BuONa, 2.) t-BuONa / 1.) toluene, 90 deg C, 6 h, 2.) 12 h
2: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 15 min, 2.) -78 deg C, 1 h; room temperature, 3 h
3: 1.) 9-BBN, 2.) aq. NaOH, aq. H2O2 / 1.) THF, room temperature, 24 h, 2.) 50 deg C, 2 h
4: 96 percent / imidazole / dimethylformamide; CH2Cl2 / 1.5 h / Ambient temperature
5: 87 percent / NBS / dimethylformamide / Ambient temperature
6: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 10 min, 2.) -78 deg C, 15 min; room temperature, 2 h
With
1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; tris(dibenzylideneacetone)dipalladium (0); dihydrogen peroxide; tert.-butyl lithium; sodium t-butanolate;
In
dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo981707v