Multi-step reaction with 8 steps
1: 87 percent / Bu4NCl, Bu2SnO / toluene / 24 h / 35 °C
2: 87 percent / pyridine / 20 h / Ambient temperature
3: 85 percent / Bu3SnH, AIBN / toluene / 23 h / Heating
4: 65 percent / DDQ, 18-crown-6, NaHSO4, moist molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 70 °C
5: 66 percent / AgOTf, collidine, molecular sieves AW-300 / CH2Cl2 / 1.) -60 deg C, 30 min, 2.) r.t., 11 h
6: H2 / 10percent Pd/C / acetic acid / 10 h
7: 98 percent / pyridine / Ambient temperature
8: 91 percent / CF3COOH / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) 10 deg C, 30 min
With
pyridine; 2,3,5-trimethyl-pyridine; sodium hydrogen sulfate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; 4 A molecular sieve; tetrabutyl-ammonium chloride; hydrogen; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
dichloromethane; acetic acid; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo00127a042