1: in toluene T=-10 - 0°C; 2 h; 2: With water; acetic acid in toluene T=10°C;

1: in tetrahydrofuran; toluene T=0 - 10°C; 1.5 h; 2: With ammonium acetate; water in tetrahydrofuran; toluene 1 h;

acetic acid in tetrahydrofuran; hexane; toluene

vinyl-magnesium bromide in tetrahydrofuran T=0 - 5°C; 1 h;

in tetrahydrofuran; toluene T=0 - 5°C; 1 h; Yields of byproduct given;

1: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 2: 87.1 percent / (-)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

1: 83 percent / Et3N / Pd(OAc)2 / acetonitrile / 12 h / Heating 2: 87.1 percent / (+)-α-pinene, chloroborane-methyl sulfide, diisopropylethylamine / hexane; tetrahydrofuran / 1) -20 deg C, 3.5 h, 2) to 0 deg C, 1 h View Scheme

1.1: sodium acetate; tetrabutylammomium bromide / palladium diacetate / toluene; 1-methyl-pyrrolidin-2-one / 120 °C / Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 20 °C 3.1: benzo[1,3,2]dioxaborole; (R)-(+)-o-tolyl-CBS-oxazaborolidine / dichloromethane / -50 - -40 °C / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 5.1: 1-methyl-pyrrolidin-2-one / 0 - 20 °C / Inert atmosphere 6.1: sodium hydroxide; water / 2-methyl tetrahydrofuran; methanol / 2 h / 70 - 80 °C / Inert atmosphere 6.2: 20 °C View Scheme

tetrabutylammomium bromide; triethylamine; palladium diacetate in toluene T=80°C; 6 h; Product distribution / selectivity;

lithium chloride; palladium diacetate in hexane; ethyl acetate; N,N-dimethyl-formamide; toluene