polystyrene-supported GaCl3 in dichloromethane T=20°C; 0.416667 h;

1: With 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene T=80°C; 6 h; 2: With potassium fluoride in tetrahydrofuran 2 h;

1.1: NBS; benzoyl peroxide / CCl4 / 10 h / 80 °C 1.2: LAH / diethyl ether / 0.5 h / 0 °C 1.3: 2.01 g / TsOH / CH2Cl2 / 0.5 h / 0 °C 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: 73 percent / dimethylformamide / 10 h / 20 °C 3.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 75 percent / 1,2-diiodoethane / hexane; tetrahydrofuran / -78 - 20 °C 4.1: Bu3SnH; AIBN / benzene / 6 h / 80 °C 4.2: 75 percent / aq. KF / tetrahydrofuran / 2 h View Scheme

1.1: 86 percent / H2SO4 / 10 h / 60 °C 2.1: NBS; benzoyl peroxide / CCl4 / 10 h / 80 °C 2.2: LAH / diethyl ether / 0.5 h / 0 °C 2.3: 2.01 g / TsOH / CH2Cl2 / 0.5 h / 0 °C 3.1: NaH / dimethylformamide / 1 h / 20 °C 3.2: 73 percent / dimethylformamide / 10 h / 20 °C 4.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 75 percent / 1,2-diiodoethane / hexane; tetrahydrofuran / -78 - 20 °C 5.1: Bu3SnH; AIBN / benzene / 6 h / 80 °C 5.2: 75 percent / aq. KF / tetrahydrofuran / 2 h View Scheme

1.1: NBS; benzoyl peroxide / CCl4 / 10 h / 80 °C 1.2: LAH / diethyl ether / 0.5 h / 0 °C 1.3: 2.01 g / TsOH / CH2Cl2 / 0.5 h / 0 °C 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: 73 percent / dimethylformamide / 10 h / 20 °C 3.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 75 percent / 1,2-diiodoethane / hexane; tetrahydrofuran / -78 - 20 °C 4.1: Bu3SnH; AIBN / benzene / 6 h / 80 °C 4.2: 75 percent / aq. KF / tetrahydrofuran / 2 h View Scheme

1.1: NaH / dimethylformamide / 1 h / 20 °C 1.2: 73 percent / dimethylformamide / 10 h / 20 °C 2.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 75 percent / 1,2-diiodoethane / hexane; tetrahydrofuran / -78 - 20 °C 3.1: Bu3SnH; AIBN / benzene / 6 h / 80 °C 3.2: 75 percent / aq. KF / tetrahydrofuran / 2 h View Scheme

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 75 percent / 1,2-diiodoethane / hexane; tetrahydrofuran / -78 - 20 °C 2.1: Bu3SnH; AIBN / benzene / 6 h / 80 °C 2.2: 75 percent / aq. KF / tetrahydrofuran / 2 h View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene T=80°C; 8 h; Product distribution; Further Variations:Reagentsalso in solid phase;

AuBr3 in acetonitrile T=25°C; 12 h;

trichloroisocyanuric acid in methanol T=20°C; 4 h;