1.1: K2CO3 / acetone / 15 h / Heating 2.1: 1.53 g / acetone / 3 h / Heating 3.1: 98 percent / CuI; Et3N / PdCl2(PPh3)2 / dimethylformamide / 1 h / 20 °C 4.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 5.1: 96 percent / CuI; i-Pr2NH / PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 60 °C 6.1: 71 percent / K2CO3; CuCl2*2H2O; NaOAc / PdCl2(PPh3)2 / 48 h / 20 °C 7.1: 72 percent / BBr3 / CH2Cl2 / 30.5 h / -78 - -40 °C 8.1: KOH / tetrahydrofuran / 2 h / Heating 8.2: 53 percent / TsOH*H2O / tetrahydrofuran / 5 h / 60 °C View Scheme

1: 1.) Pd2(dba)3, triphenylarsine / 1.) dioxane, 10 min, 2.) 24 h, 50 deg C 2: 98 percent / HOAc, NaOAc, KF / 2 h / 110 °C 3: 1.) H2, 2.) glacial acetic acid, conc. H2SO4 / 1.) Raney-Ni / 1.) methanol, 2.) 120 deg C, 2.5 h View Scheme

1: 78 percent / tris(dibenzylideneacetone)dipalladium, AsPh3 / dioxane / 48 h / 50 °C 2: H2, aq. EtOH / Ra-Ni / 760 Torr 3: glacial acetic acid, conc. aq. HCl / 1.5 h / 100 °C View Scheme

1: 67 percent / tris(dibenzylideneacetone)dipalladium, AsPh3 / dioxane / 48 h / 50 °C / 1.) dioxane, 20 deg C, 15 min, 2.) dioxane, 50 deg C, 48 h 2: H2, aq. EtOH / Ra-Ni / 760 Torr 3: glacial acetic acid, conc. aq. HCl / 1.5 h / 100 °C View Scheme

1: K2CO3 / acetone / 15 h / Heating 2: 1.53 g / acetone / 3 h / Heating 3: 98 percent / CuI; Et3N / PdCl2(PPh3)2 / dimethylformamide / 1 h / 20 °C 4: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 5: 96 percent / CuI; i-Pr2NH / PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 60 °C 6: 81 percent / DIBAL-H / toluene; CH2Cl2 / 3 h / -78 °C 7: 67 percent / TBAF / tetrahydrofuran / 3 h / Heating 8: 78 percent / NaOMe / methanol / 20 h / Heating View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '5722126', constants.ctx, '0')">PhCH₂PPh₃ClO₄</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8127929', constants.ctx, '0')">potassium iodide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />0.3&nbsp;h;&nbsp;&nbsp;Reflux;&nbsp;&nbsp;regioselective reaction;&nbsp;<br /> &nbsp;

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