tetrakis(triphenylphosphine) palladium(0) in toluene Stille cross-coupling; 24 h; Heating;

1.1: 80 percent / KOtBu; 18-crown-6 / tetrahydrofuran / 24 h / Heating 2.1: BuLi / diethyl ether; tetrahydrofuran / 1 h / -78 °C 2.2: 68 percent / diethyl ether; tetrahydrofuran / -78 - 20 °C 3.1: 84 percent / ICl / CH2Cl2 / -70 - -40 °C 4.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 4.2: triisopropyl borate / diethyl ether; hexane / -78 - 20 °C 5.1: dioxane 6.1: (Ph3P)4Pd / toluene / 24 h / Heating View Scheme

1.1: BuLi / diethyl ether; tetrahydrofuran / 1 h / -78 °C 1.2: 68 percent / diethyl ether; tetrahydrofuran / -78 - 20 °C 2.1: 84 percent / ICl / CH2Cl2 / -70 - -40 °C 3.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 3.2: triisopropyl borate / diethyl ether; hexane / -78 - 20 °C 4.1: dioxane 5.1: (Ph3P)4Pd / toluene / 24 h / Heating View Scheme

1.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 1.2: triisopropyl borate / diethyl ether; hexane / -78 - 20 °C 2.1: dioxane 3.1: (Ph3P)4Pd / toluene / 24 h / Heating View Scheme

1.1: 84 percent / ICl / CH2Cl2 / -70 - -40 °C 2.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 2.2: triisopropyl borate / diethyl ether; hexane / -78 - 20 °C 3.1: dioxane 4.1: (Ph3P)4Pd / toluene / 24 h / Heating View Scheme

Yield given. Multistep reaction;