<b>Multi-step reaction with 6 steps<br /> </b>1: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature<br />2: SOCl₂ / toluene / 1.25 h<br />3: AlCl₃ / CS₂ / 16 h / Ambient temperature<br />4: TiCl₄ / toluene / 17 h / Ambient temperature<br />5: sodium borohydride / methanol / 1.5 h / Ambient temperature<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8127929', constants.ctx, '0')">potassium iodide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '12591084', constants.ctx, '0')">[{(η⁵-C₅Me₅)IrCl}₂(μ-Cl)₂]</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=80&deg;C;&nbsp;1.5&nbsp;h;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8127929', constants.ctx, '0')">potassium iodide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '12591084', constants.ctx, '0')">[{(η⁵-C₅Me₅)IrCl}₂(μ-Cl)₂]</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=80&deg;C;&nbsp;1.5&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3571228', constants.ctx, '0')">tetra(n-butyl)ammonium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=80&deg;C;&nbsp;48&nbsp;h;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '9054647', constants.ctx, '0')">1-(3,4-dichlorophenyl)-1,2-dihydronaphthalene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '972072', constants.ctx, '0')">benzo[1,3,2]dioxaborole</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '6664856', constants.ctx, '0')">(S)-QUINAP</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;12&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587207', constants.ctx, '0')">diethylzinc</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=20&deg;C;&nbsp;2&nbsp;h;&nbsp;<br />Stage #3: <a href="#" onclick="return RXDsubstances(event, this, '1730793', constants.ctx, '0')">N-chloro-N-methylamine</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=0&deg;C;&nbsp;0.0833333&nbsp;h;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '19585343', constants.ctx, '0')">R,S-[Ir(1,5-cyclooctadiene)(PPh₂(C₉H₁₀)(C₃H₃NO-i-Bu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a> <br />T=20&deg;C;&nbsp;P=15201&nbsp;Torr;&nbsp;12&nbsp;h;&nbsp;&nbsp;optical yield given as percent eeenantioselective reaction;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '19585342', constants.ctx, '0')">C₃₂H₁₂BF₂₄^(1-)*C₃₆H₄₄IrNOP⁽¹⁺⁾</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a> <br />T=20&deg;C;&nbsp;P=15201&nbsp;Torr;&nbsp;12&nbsp;h;&nbsp;&nbsp;optical yield given as percent eeenantioselective reaction;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: catecholborane / (S)-QUINAP-Rh / toluene / 2 h / 20 &deg;C<br />1.2: aq. H₂O₂; flash silica / hexane / 1 h / 0 &deg;C<br />2.1: catecholborane / (S)-QUINAP-Rh / CH₂Cl₂ / 12 h / 20 &deg;C<br />2.2: ZnEt₂ / toluene / 2 h / 20 &deg;C<br />2.3: H₂O; diethyl ether / 0.08 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: potassium tert-butoxide / 2-methyl-propan-2-ol / 16 h / Heating<br />2: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating<br />3: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature<br />4: SOCl₂ / toluene / 1.25 h<br />5: AlCl₃ / CS₂ / 16 h / Ambient temperature<br />6: TiCl₄ / toluene / 17 h / Ambient temperature<br />7: sodium borohydride / methanol / 1.5 h / Ambient temperature<br /> <br /> &nbsp;