4-(N,N-dimethlyamino)pyridine; oxygen; sodium carbonate; Pd(II) N-heterocyclic carbene in toluene T=80°C; intramolecular Wacker cyclisation; 12 h; Product distribution; Further Variations:CatalystsSolvents;

tetrabutyl-ammonium chloride; sodium carbonate; palladium diacetate in N,N-dimethyl-formamide T=100°C; 24 h; Yield given. Yields of byproduct given;

sodium in diethyl ether Substitution; cyclization; 4.5 h; Heating;

phenyl isocyanate 16 h; Heating;

1: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 2: BunLi, <Ph3PMe>+Br- / 1) Et2O, hexane, r.t., 4 h, 2) Et2O, 40 deg C, 19 h View Scheme

1: di-μ-acetato-bis<(3,2,10-η-cis-4-acetoxypinene)palladium(II), Cu(OAc)2, O2 / methanol / 13 h / 35 °C 2: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 3: BunLi, <Ph3PMe>+Br- / 1) Et2O, hexane, r.t., 4 h, 2) Et2O, 40 deg C, 19 h View Scheme

1: BuLi / 1)hexane, -78 deg C, 2) -78 deg C to r.t. 2: di-μ-acetato-bis<(3,2,10-η-cis-4-acetoxypinene)palladium(II), Cu(OAc)2, O2 / methanol / 31 h / 35 °C 3: 17 percent / CF3CO2H / CCl4 / 24 h / Ambient temperature 4: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 5: BunLi, <Ph3PMe>+Br- / 1) Et2O, hexane, r.t., 4 h, 2) Et2O, 40 deg C, 19 h View Scheme

1: di-μ-acetato-bis<(3,2,10-η-cis-4-acetoxypinene)palladium(II), Cu(OAc)2, O2 / methanol / 31 h / 35 °C 2: 17 percent / CF3CO2H / CCl4 / 24 h / Ambient temperature 3: 48 percent / Pd(OCOCF3)(OOBut), ButOOH / benzene / 16 h / 50 °C 4: BunLi, <Ph3PMe>+Br- / 1) Et2O, hexane, r.t., 4 h, 2) Et2O, 40 deg C, 19 h View Scheme

1: 95 percent / m-chloroperbenzoic acid / CHCl3 / 0.17 h / 0 °C 2: 75 percent / 3percent NaOMe / methanol / 1.5 h 3: 85 percent / NaOAc / 2 h / Heating 4: 0.33 h / 320 °C View Scheme

1: 75 percent / 3percent NaOMe / methanol / 1.5 h 2: 85 percent / NaOAc / 2 h / Heating 3: 0.33 h / 320 °C View Scheme