sodium tetrahydroborate

1.1: DIBAL-H / hexane; toluene / 4 h / 0 - 20 °C 1.2: 92 percent / I2 / tetrahydrofuran; hexane; toluene / -78 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: 100 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 100 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 1.2: 87 percent / tetrahydrofuran; benzene; hexane / 2 h / 20 °C 2.1: DIBAL-H / hexane; toluene / 4 h / 0 - 20 °C 2.2: 92 percent / I2 / tetrahydrofuran; hexane; toluene / -78 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 3.2: 100 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -78 °C 1.2: 84 percent / selenium / tetrahydrofuran; pentane / -78 - 20 °C 2.1: Br2 / tetrahydrofuran; benzene / 0.75 h / 0 - 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 3.2: 87 percent / tetrahydrofuran; benzene; hexane / 2 h / 20 °C 4.1: DIBAL-H / hexane; toluene / 4 h / 0 - 20 °C 4.2: 92 percent / I2 / tetrahydrofuran; hexane; toluene / -78 - 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 5.2: 100 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

1.1: Br2 / tetrahydrofuran; benzene / 0.75 h / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 2.2: 87 percent / tetrahydrofuran; benzene; hexane / 2 h / 20 °C 3.1: DIBAL-H / hexane; toluene / 4 h / 0 - 20 °C 3.2: 92 percent / I2 / tetrahydrofuran; hexane; toluene / -78 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 4.2: 100 percent / BF3*OEt2 / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

Multistep reaction;

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