1.1: 92 percent / CH2Cl2 / Heating 2.1: KHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 2.2: 79 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C 4.1: 75 percent / trifluoroacetylrhenium(VII) oxide; 2,6-lutidine / tetrahydrofuran / 8 h / 0 - 20 °C 5.1: 90 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 6.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 7.1: 81 percent / pyridine / 3 h / Heating 8.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 9.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 10.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 11.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 12.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 13.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 14.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 14.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 15.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 16.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103853', constants.ctx, '0')">1H-imidazole</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />Substitution;&nbsp;iodination;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: LiAlH₄ / diethyl ether / 0 &deg;C<br />2: triphenylphosphine, imidazole, iodine / toluene / 3 h / 60 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 95 percent / tetrahydrofuran / 0 &deg;C<br />2: 90 percent / propionic acid / Heating<br />3: LiAlH₄ / diethyl ether / 0 &deg;C<br />4: triphenylphosphine, imidazole, iodine / toluene / 3 h / 60 &deg;C<br /> <br /> &nbsp;