Multi-step reaction with 8 steps
1: 90 percent / p-TsOH / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) r.t., 1 h
2: PPh3, piperidine / Pd(PPh3)2Cl2, CuI / 1.) r.t., 2 d, 2.) 55 deg C, 2 d
3: PPh3, piperidine / Pd(PPh3)2Cl2, CuI / 96 h / 55 °C
4: 95 percent / NaOH / tetrahydrofuran; methanol / 0.75 h / Ambient temperature
5: 94 percent / PPh3, piperidine / Pd(PPh3)2Cl2, CuI / 1.) r.t., 1 h, 2.) 35 deg C, overnight
6: 82 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
7: 86 percent / PPh3, piperidine / Pd(PPh3)2Cl2, CuI / 1.) r.t., 1 h, 2.) 35 deg C, overnight
8: 92 percent / NaOH, H2O / tetrahydrofuran; methanol / 2 h / Ambient temperature
With
piperidine; sodium hydroxide; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; triphenylphosphine;
bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/(SICI)1521-3765(19981204)4:12<2423::AID-CHEM2423>3.0.CO;2-8