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Reagents and conditions: (i) sealed tube, 1,4-dioxane, CuI (5.0 mol %), NaI, racemic trans-N,N′-dimethyl-1,2-cyclohexanediamine (10 mol %), 110 °C, N2, 24 h; (ii) DMSO, bis(pinacolato)diboron, KOAc, PdCl2(dppf)·CH2Cl2, 90 °C, N2, 4 h; (iii) toluene/EtOH, 2 M Na2CO3, PdCl2(dppf)·CH2Cl2, 85–90 °C, N2, 1.5 h.
