1.1: thionyl chloride / dichloromethane / 9 h / 0 °C / |Inert atmosphere; |Reflux 2.1: dimethyl sulfoxide / 2 h / 140 °C / |Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 21 h / |Inert atmosphere; |Reflux 4.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 5.2: -95 - -30 °C / |Inert atmosphere 5.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 6.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 7.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme

1.1: dimethyl sulfoxide / 2 h / 140 °C / |Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 21 h / |Inert atmosphere; |Reflux 3.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 4.2: -95 - -30 °C / |Inert atmosphere 4.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 5.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 6.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 21 h / |Inert atmosphere; |Reflux 2.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 3.2: -95 - -30 °C / |Inert atmosphere 3.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 4.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 5.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme

1.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 2.2: -95 - -30 °C / |Inert atmosphere 2.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 3.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 4.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme