1: trimethylaluminum; (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-yne With methyl aluminoxane; rac-ethylenebis(1-indenyl)zirconium(IV) chloride in toluene T=20°C; Negishi carboalumination; 8 h; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With NiCl2((PPh3)P)2; n-butyllithium in tetrahydrofuran T=-20°C; 2 h;

ceric ammoniumnitrate in dichloromethane; water; acetonitrile

1: 95 percent / potassium tert-butoxide / dimethylformamide / -20 deg C, 2 h then room temp., 1 h 2: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 3: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 4: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 5: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 67 percent / mCPBA / CH2Cl2 2: 91 percent / Al(O-i-Pr)3 / toluene / 110 °C 3: 98 percent / diethylaniline, pyridine / benzene 4: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 5: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 6: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 7: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 91 percent / Al(O-i-Pr)3 / toluene / 110 °C 2: 98 percent / diethylaniline, pyridine / benzene 3: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 4: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 5: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 6: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 98 percent / diethylaniline, pyridine / benzene 2: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 3: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 4: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 5: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 2: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 2: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 3: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 2: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 3: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 4: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

1: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 2: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 3: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 4: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme