dichloro bis(acetonitrile) palladium(II); copper(l) iodide in acetonitrile Inert atmosphere;

CuI in n-heptane; 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran; ethyl acetate; acetonitrile

1.1: N-bromosuccinmide / ethyl acetate / 22 °C 2.1: Zn(ClO4)2-2H2O / toluene / 20 - 80 °C / Molecular sieve 2.2: 30 °C / 750.08 Torr 3.1: sodium hydrogencarbonate / ethyl acetate 3.2: 20 °C 3.3: 80 °C / Inert atmosphere 4.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere View Scheme

1.1: Zn(ClO4)2-2H2O / toluene / 20 - 80 °C / Molecular sieve 1.2: 30 °C / 750.08 Torr 2.1: sodium hydrogencarbonate / ethyl acetate 2.2: 20 °C 2.3: 80 °C / Inert atmosphere 3.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere View Scheme

1.1: potassium hydroxide / methanol / 5 - 25 °C 1.2: 0.5 h 2.1: sodium hydrogencarbonate / ethyl acetate 2.2: 20 °C 2.3: 80 °C / Inert atmosphere 3.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere View Scheme

1.1: sodium hydrogencarbonate / ethyl acetate 1.2: 20 °C 1.3: 80 °C / Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere View Scheme

1.1: sodium hydrogencarbonate / ethyl acetate 1.2: 20 °C 1.3: 80 °C / Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / Inert atmosphere View Scheme

1.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 1.2: 16 h / 25 °C 2.1: potassium hydroxide / methanol / 25 °C 3.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 3.2: 16 h / 80 °C / |Large scale 4.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale View Scheme

1.1: hydrogenchloride / water / 16 h 2.1: magnesium / tetrahydrofuran / 3.5 h / |Inert atmosphere 2.2: 16 h / 25 °C 3.1: potassium hydroxide / methanol / 25 °C 4.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 4.2: 16 h / 80 °C / |Large scale 5.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale View Scheme

1.1: palladium diacetate; 1,4-di(diphenylphosphino)-butane; potassium carbonate / acetonitrile / 1 h / |Inert atmosphere; |Large scale 1.2: 16 h / 80 °C / |Large scale 2.1: dichloro bis(acetonitrile) palladium(II) / acetonitrile / 20 - 80 °C / |Inert atmosphere; |Large scale View Scheme