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Reagents and conditions: (a)219o-bromoaniline, KOt-Bu, neat, 120 °C, 24 h, 81%; (b) o-aminothiophenol, CuI, l-proline, Cs2CO3, CTAB, 3:1 toluene/H2O, reflux, overnight, 97%; (c) Pd(OAc)2, P(t-Bu)3·HBF4, Cs2CO3, DMF, 150 °C, 24 h, 51%; (d) isopentyl nitrite, 1:1 DCM/AcOH, 0 °C, 1 h, then hydroquinone, rt, 30 min, 70%.
