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Reagents and conditions: (a) (i) NaNO2, HCl, CH3COOH; (ii) SO2, CH3COOH; (b) 7, Et3N, DCM, rt; (c) phenyl boronic acid, Pd(PPh3)4, CsF, 1,4-dioxane, reflux, 69%; (d) pyridine-N-oxide, PtBu3·HBF4, Pd(OAc)2, K2CO3, toluene, 110 °C, 38%; (e) iron dust, 0.1 M CH3COOH.
