[(P{(C6H11)3})2Pd(Cl)2]; Miyaura reagent in various solvent(s) T=100°C; 18 h; other borane-reagent, solvent, and catalyst; Product distribution;

1.1: 58 percent / triphenylphosphine; zinc / bis(triphenylphosphine)nickel bromide / acetonitrile / 1.5 h / 65 °C 2.1: aq. ammonia; hydrogen / Raney nickel / methanol / 3 h / pH 9 3.1: aq. HCl; sodium nitrite / dioxane / 1.5 h / pH 3 / Heating 3.2: 618 mg / aq. NaHCO3 / dioxane 4.1: 74 percent / triphenylphosphine; N-bromosuccinimide / tetrahydrofuran / 0 - 20 °C 5.1: 83 percent / sodium sulfite; H2O / dioxane / 1 h / Heating 6.1: aq. sodium carbonate / acetonitrile / 16 h / 20 °C 7.1: CH2Cl2; H2O / 2 h / 20 °C 8.1: 100.0 mg / triethylamine / H2O; acetonitrile / 0.5 h / 20 °C / pH 8.5 - 9.0 View Scheme

4-(N,N-dimethlyamino)pyridine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane in 1,4-dioxane T=80°C; 16 - 24 h; Inert atmosphere;

palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine in dimethyl sulfoxide T=70°C; 25 h; Yield given;

1: Pd(OAc)2, 1,3-bis(diphenylphosphino)propane, Et3N / dimethylsulfoxide / 25 h / 70 °C 2: 71 percent / NaOH aq. / ethanol / Ambient temperature View Scheme

potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in toluene T=85 - 90°C; 2 h; other arylboronic acids; Product distribution;

Multi-step reaction with 2 steps 1: 80 percent / methylmorpholine, Pd(O)(PPh3)4 / acetonitrile / 15 h / 70 °C2: 72 percent / 1M NaOH / dimethylformamide / 2.25 h / 0 - 20 °C  

Multi-step reaction with 4 steps 1: 85 percent / 1,3-bis(diphenylphosphino)propane; Et3N; trioctylsilane / Pd(OAc)2 / dimethylformamide / 4 h / 70 °C2: 91 percent / NaBH4 / CH2Cl2; methanol / 0.5 h / 20 °C3: NaOH / methanol; H2O / 4 h / 20 °C4: HCl / ethyl acetate / 3 h / 20 °C  

Stage #1: With  1,3-bis-(diphenylphosphino)propane; palladium diacetate in  water; N,N-dimethyl-formamide T=70°C; 0.166667 h; Stage #2: With  N,N'-di-isopropylethylenediamine T=70°C; 3 h;