1.1: bis-triphenylphosphine-palladium(II) chloride; formic acid; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere View Scheme

1.1: B(OAc)3; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 72 h / 20 °C / Inert atmosphere 2.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; formic acid; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / 3 h / -78 °C / Inert atmosphere 4.2: Inert atmosphere View Scheme

1.1: manganese(IV) oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: B(OAc)3; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere 5.1: bis-triphenylphosphine-palladium(II) chloride; formic acid; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere 6.1: boron tribromide / dichloromethane / 3 h / -78 °C / Inert atmosphere 6.2: Inert atmosphere View Scheme

1.2: 78 percent / Jones reagent 2.1: 81 percent / TMSI View Scheme

1.1: 55 percent / AgO 2.2: 78 percent / Jones reagent 3.1: 81 percent / TMSI View Scheme

1.1: 62 percent / tBuN=P[N=P(NMe2)3]3 2.1: 55 percent / AgO 3.2: 78 percent / Jones reagent 4.1: 81 percent / TMSI View Scheme