Suzuki coupling;

N-bromosuccinmide; hydrogen bromide in water; acetonitrile 3 h; Ambient temperatureother substrates, other reagents;

1.1: LiAlH4 / tetrahydrofuran / 0.67 h / 0 °C 2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C 3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C 3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C 3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C 4.1: 97 percent / HCl; H2O / tetrahydrofuran / 0.83 h / 0 °C 5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 6.1: 90 percent / MeONa / methanol / 1 h / 0 °C 7.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 8.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 10.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 11.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 11.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 12.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 13.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 14.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 15.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 16.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 17.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 18.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 19.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 20.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 21.1: 84 percent / DMAP / benzene / 10 h / 35 °C 22.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 23.1: pyridine / 0.67 h / 20 °C 24.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 25.1: DMAP / 4 h / 100 °C 25.2: DMAP / toluene / 4 h / 100 °C 26.1: P(OMe)3 / 5 h / 110 °C 27.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 28.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 29.1: 98 percent / pyridine / 0.17 h / -23 °C 30.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 31.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 32.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 33.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 34.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 35.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 36.1: 87 percent / pyridine / 0.5 h / 20 °C 37.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 38.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C 39.1: 100 percent / HCl; H2O / ethanol / 2 h / 20 °C View Scheme

1.1: LiAlH4 / tetrahydrofuran / 0.67 h / 0 °C 2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C 3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C 3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C 3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C 4.1: 97 percent / HCl; H2O / tetrahydrofuran / 0.83 h / 0 °C 5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 6.1: 90 percent / MeONa / methanol / 1 h / 0 °C 7.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 8.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 10.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 11.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 11.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 12.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 13.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 14.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 15.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 16.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 17.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 18.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 19.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 20.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 21.1: 84 percent / DMAP / benzene / 10 h / 35 °C 22.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 23.1: pyridine / 0.67 h / 20 °C 24.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 25.1: DMAP / 4 h / 100 °C 25.2: DMAP / toluene / 4 h / 100 °C 26.1: P(OMe)3 / 5 h / 110 °C 27.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 28.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 29.1: 98 percent / pyridine / 0.17 h / -23 °C 30.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 31.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 32.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 33.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 34.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 35.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C View Scheme

lithium aluminium tetrahydride in diethyl ether

1: base View Scheme

1.1: LiAlH4 / tetrahydrofuran / 0.67 h / 0 °C 2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C 3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C 3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C 3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C 4.1: 97 percent / HCl; H2O / tetrahydrofuran / 0.83 h / 0 °C 5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 6.1: 90 percent / MeONa / methanol / 1 h / 0 °C 7.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 8.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 10.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 11.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 11.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 12.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 13.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 14.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 15.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 16.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 17.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 18.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 19.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 20.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 21.1: 84 percent / DMAP / benzene / 10 h / 35 °C 22.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 23.1: pyridine / 0.67 h / 20 °C 24.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 25.1: DMAP / 4 h / 100 °C 25.2: DMAP / toluene / 4 h / 100 °C 26.1: P(OMe)3 / 5 h / 110 °C 27.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 28.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 29.1: 98 percent / pyridine / 0.17 h / -23 °C 30.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 31.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 32.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 33.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 34.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C View Scheme

1.1: LiAlH4 / tetrahydrofuran / 0.67 h / 0 °C 2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C 3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C 3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C 3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C 4.1: 97 percent / HCl; H2O / tetrahydrofuran / 0.83 h / 0 °C 5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / 0 °C 6.1: 90 percent / MeONa / methanol / 1 h / 0 °C 7.1: 94 percent / AlH3 / toluene; tetrahydrofuran / 2 h / -78 °C 8.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C 9.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C 10.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C 11.1: s-BuLi / cyclohexane / 0.42 h / -23 °C 11.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C 12.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C 13.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C 14.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C 15.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C 16.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C 17.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C 18.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C 19.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C 20.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C 21.1: 84 percent / DMAP / benzene / 10 h / 35 °C 22.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C 23.1: pyridine / 0.67 h / 20 °C 24.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 25.1: DMAP / 4 h / 100 °C 25.2: DMAP / toluene / 4 h / 100 °C 26.1: P(OMe)3 / 5 h / 110 °C 27.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C 28.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C 29.1: 98 percent / pyridine / 0.17 h / -23 °C 30.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C 31.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C 32.1: 42 percent / DBU / toluene / 1.75 h / 50 °C 33.1: 91 percent / DMAP; pyridine / 13 h / 20 °C 34.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C 35.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C 36.1: 87 percent / pyridine / 0.5 h / 20 °C 37.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C 38.1: 76 percent / H2 / Pd(OH)2/C / ethanol / 23 h / 20 °C View Scheme

1: 97 percent / 5percent KOH / methanol; H2O 2: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 3: 59 percent / tetrahydrofuran / Ambient temperature 4: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 5: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C View Scheme

lithium aluminium tetrahydride in diethyl ether T=-10°C; 1 h;