gem-diamine piperidinomethane piperidium tetrafluoroborate in neat (no solvent) T=80°C; Michael Addition; 6 h; Inert atmosphereGreen chemistry;

palladium 10 on activated carbon; sodium carbonate; triphenylphosphine in ethylene glycol dimethyl ether T=80°C; Suzuki coupling; 16 h; Inert atmosphere;

1: With 1,4-diaza-bicyclo[2.2.2]octane in benzene 15.5 h; Heating; 2: With silica gel in benzene T=110°C; 1 h;

ethanol

1.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / acetonitrile / 10 - 15 °C / Inert atmosphere 2.2: 1.17 h / 20 °C / Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 3.2: 0.5 h / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / toluene / 0.08 h / 20 °C / Inert atmosphere 4.2: 16 h / 110 °C / Inert atmosphere 5.1: potassium tert-butylate / dimethyl sulfoxide / 0.17 h / 20 °C / Inert atmosphere View Scheme