1: methyllithium in diethyl ether T=0°C; 0.166667 h; 2: 2,3-dihydro-[1,1'-biphenyl]-4(1H)-one in diethyl ether T=-23°C; 0.333333 h; 3: With Mukayama reagent in diethyl ether T=-78°C; 0.5 h;

1.1: 86 percent / Pd(OAc)2 / acetonitrile 2.1: CuCN / diethyl ether / 0.17 h / 0 °C 2.2: diethyl ether / 0.33 h / -23 °C 2.3: 94 percent / N-tert-butylbenzenesulfinimidoyl chloride / diethyl ether / 0.5 h / -78 °C View Scheme

ammonia; sodium

1-iso-propyl-4-methylbenzene; palladium on activated charcoal

1: p-cymene / Pd-C 2: (i) aq. NaOH, (ii) KMnO4, aq. NaOH View Scheme