silver(I) acetate; sodium t-butanolate in 1,4-dioxane T=135 - 155°C;

2-(tert-butyl)-1,1,3,3-tetramethylguanidine in toluene T=80°C; 24 h; in the dark;

1: 30 percent / N-tert-butyl-N',N',N'',N''-tetramethylguanidine (BTMG) / tetrahydrofuran / 48 h / Heating 2: 33 percent / N-tert-butyl-N',N',N'',N''-tetramethylguanidine (BTMG) / tetrahydrofuran / 48 h / Heating View Scheme

1: triethylamine / toluene / 15 h / |Reflux; |Inert atmosphere 2: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 3: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 4: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 5: bis-(trifluoromethylsulphonyl)amine / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 6: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

1: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 2: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 3: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 4: potassium hydrogen difluoride / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux 6: triethylamine / toluene / 15 h / |Reflux; |Inert atmosphere 7: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 8: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 9: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 10: bis-(trifluoromethylsulphonyl)amine / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 11: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

1: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 2: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 3: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 4: bis-(trifluoromethylsulphonyl)amine / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux 2: triethylamine / toluene / 15 h / |Reflux; |Inert atmosphere 3: dimethylsulfide borane complex / dichloromethane / 2 h / 0 °C / |Inert atmosphere 4: toluene / 1 h / 20 °C / |Schlenk technique; |Inert atmosphere 5: toluene; o-di-fluorobenzene / 16 h / 140 °C / |Inert atmosphere 6: bis-(trifluoromethylsulphonyl)amine / toluene; methanol; water / 2 h / 0 - 20 °C / |Schlenk technique; |Sealed tube; |Cooling; |Inert atmosphere 7: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; water; ethanol / 80 °C / |Inert atmosphere; |Sonication; |Reflux View Scheme

trifluoroacetic acid in chloroform-d1 0.25 h; Ambient temperature;

2-(tert-butyl)-1,1,3,3-tetramethylguanidine in tetrahydrofuran 48 h; Heating;

1: 52 percent / 3,5-dinitrobenzoic acid (3,5-DNPBA) / CH2Cl2 / 2 h / Ambient temperature 2: 72 percent / 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / tetrahydrofuran / 4.5 h / 0 - 20 °C 3: 100 percent / trifluoroacetic acid (TFA) / CDCl3 / 0.25 h / Ambient temperature; other solvents, var. pH, var. reaction times View Scheme