potassium carbonate in N,N-dimethyl-formamide T=23°C; 1 h;

sulfuryl dichloride in diethyl ether T=0°C;

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 2.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 3.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 3.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 4.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 5.1: aq. H2O2 / toluene / 3 h 6.1: toluene / 1 h / 80 °C 7.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 8.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 9.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 98 percent / nBu4NF / tetrahydrofuran / 6 h / 23 °C 2.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 3.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 4.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 4.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 5.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 6.1: aq. H2O2 / toluene / 3 h 7.1: toluene / 1 h / 80 °C 8.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 9.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 10.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 2.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 3.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 3.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 4.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 5.1: aq. H2O2 / toluene / 3 h 6.1: toluene / 1 h / 80 °C 7.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 8.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 9.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 2.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 2.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 3.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 4.1: aq. H2O2 / toluene / 3 h 5.1: toluene / 1 h / 80 °C 6.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 7.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 8.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 1.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 2.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 3.1: aq. H2O2 / toluene / 3 h 4.1: toluene / 1 h / 80 °C 5.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 6.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 7.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: Me3OBF4 / CH2Cl2 / 0 - 23 °C 1.2: 80 percent / DBU / CH2Cl2 / 4 h / 0 °C 2.1: 98 percent / nBu4NF / tetrahydrofuran / 6 h / 23 °C 3.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 4.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 5.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 5.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 6.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 7.1: aq. H2O2 / toluene / 3 h 8.1: toluene / 1 h / 80 °C 9.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 10.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 11.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 97 percent / DBU / CH2Cl2 / 8 h / 0 °C 2.1: 98 percent / nBu4NF / tetrahydrofuran / 6 h / 23 °C 3.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 4.1: 91 percent / EtiPr2N; TBAI / dimethylformamide / 3 h / 80 °C 5.1: LDA / tetrahydrofuran / -78 °C 5.2: 81 percent / tetrahydrofuran / cooling 6.1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 7.1: 249 mg / toluene / 1 h / 80 °C 8.1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 9.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 10.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 11.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 2: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 3: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme