Multi-step reaction with 5 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 deg C to 0 deg C
2: 58 percent / AlCl3, tert-butylamine-borane / toluene / 2 h / 5 °C
3: 99 percent / trifluoroacetic acid, triethylsilane / 1.) 5 deg C, 60 min, 2.) RT, 18 h
4: 98 percent / ethanethiol, lithium hydride / dimethylformamide / 3 h / Heating
5: 1.) phenylboronic acid, propionic acid, 2.) AlCl3, tert-butylamine-borane / 1.) toluene, reflux, 4 h, 2.) CH2Cl2, 0 deg C, 2 h
With
triethylsilane; n-butyllithium; aluminium trichloride; lithium hydride; borane tert-butylamine; propionic acid; trifluoroacetic acid; ethanethiol; phenylboronic acid;
In
N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00085a019