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<p class="MsoTitle" style="margin:0cm;margin-bottom:.0001pt"><span lang="EN-US" style="font-size:18.0pt;font-family:"Verdana","sans-serif";color:black;font-weight:normal"><o:p> </o:p></span></p>
<p class="MsoTitle" style="margin:0cm;margin-bottom:.0001pt"><span lang="EN-US" style="font-size:14.0pt;font-family:"Verdana","sans-serif";color:black;font-weight:normal">VABILO NA PREGLOV KOLOKVIJ / INVITATION TO THE PREGL COLLOQUIUM<o:p></o:p></span></p>
<p class="MsoNormal"><b><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Verdana","sans-serif""><o:p> </o:p></span></b></p>
<p align="center" style="margin:0cm;margin-bottom:.0001pt;text-align:center"><b><span style="font-size:18.0pt;font-family:"Verdana","sans-serif";mso-fareast-language:SL">Dr.
</span></b><b><span style="font-size:18.0pt;font-family:"Verdana","sans-serif"">Dominique Cahard</span></b><b><span lang="EN-US" style="font-size:18.0pt;font-family:"Verdana","sans-serif";mso-fareast-language:SL"><o:p></o:p></span></b></p>
<p class="MsoNormal" align="center" style="text-align:center;text-autospace:none">
<span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Verdana","sans-serif";mso-fareast-language:EN-US">UMR 6014 CNRS COBRA, University et INSA de Rouen, 76821 Mont St. Aignan, France;
</span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Verdana","sans-serif"">E-mail:
<a href="mailto:dominique.cahard@univ-rouen.fr">dominique.cahard@univ-rouen.fr</a></span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Verdana","sans-serif";mso-fareast-language:FR"><o:p></o:p></span></p>
<p class="MsoNormal" align="center" style="text-align:center;line-height:150%"><b><span lang="EN-US" style="font-size:14.0pt;line-height:150%;font-family:"Verdana","sans-serif""><o:p> </o:p></span></b></p>
<p class="MsoNormal" align="center" style="text-align:center;line-height:150%"><b><span lang="EN-US" style="font-size:14.0pt;line-height:150%;font-family:"Verdana","sans-serif"">Èetrtek, Thursday, 5. 6. 2014, ob / at 13h</span></b><b><span lang="EN-US" style="font-size:14.0pt;line-height:150%;font-family:"Verdana","sans-serif";mso-fareast-language:FR"><o:p></o:p></span></b></p>
<h6 style="mso-margin-top-alt:0cm;margin-right:0cm;margin-bottom:6.0pt;margin-left:0cm">
<b><span lang="EN-US" style="font-size:11.0pt;font-family:"Verdana","sans-serif"">Velika predavalnica Kemijskega in¹tituta / Lecture Hall at the National Institute of Chemistry; Hajdrihova 19, Ljubljana</span></b><b><span lang="EN-US" style="font-size:12.0pt;font-family:"Verdana","sans-serif"">
<o:p></o:p></span></b></h6>
<p class="MsoNormal" style="mso-margin-top-alt:6.0pt;margin-right:0cm;margin-bottom:6.0pt;margin-left:0cm;text-align:justify">
<b><span lang="EN-US" style="font-size:9.0pt;line-height:115%;font-family:"Verdana","sans-serif";color:#993366"><o:p> </o:p></span></b></p>
<p class="MsoNormal" align="center" style="margin-bottom:12.0pt;text-align:center;text-autospace:none">
<b><span lang="EN-US" style="font-size:16.0pt;line-height:115%;font-family:"Verdana","sans-serif";color:#6E0763;mso-fareast-language:EN-US">Enantioselective Metal-Catalyzed Hydrogen Transfer Reactions for the Construction of CF<sub>3</sub>-bearing Stereogenic
Carbons<o:p></o:p></span></b></p>
<p class="MsoNormal" style="margin-bottom:12.0pt;text-align:justify;text-autospace:none">
<span lang="EN-US" style="font-size:12.0pt;line-height:115%;mso-fareast-language:EN-US">The synthesis of enantiopure molecules featuring a trifluoromethyl motif at a stereogenic carbon centre increasingly stimulates high interest in many laboratories. Such
compounds can be approached by direct introduction of the CF<sub>3</sub> group or by exploitation of prochiral trifluoromethylated substrates.<sup>[1]</sup> The stereoselective construction of all-C tertiary CF<sub>3</sub>-bearing stereogenic carbon centres
without any heteroatom substituent undoubtedly belongs to the most fundamental topics in fluorine chemistry and remains highly challenging. As tool for this purpose, we have investigated the ruthenium catalyzed redox isomerization of trifluoromethylated allylic
alcohols to access enantioenriched </span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:Symbol;mso-fareast-language:EN-US">b</span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;mso-fareast-language:EN-US">-trifluoromethyl</span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:Symbol;mso-fareast-language:EN-US">
</span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;mso-fareast-language:EN-US">carbonyl compounds. The catalytic redox isomerization is an efficient, selective, atom-economic, one-step process for isomerization of C=C bond of
</span><i><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Times","serif";mso-fareast-language:EN-US">O-allylic
</span></i><span lang="EN-US" style="font-size:12.0pt;line-height:115%;mso-fareast-language:EN-US">substrates into saturated carbonyl compounds.<sup>[2]</sup> In this method, a transition metal assists the migration of the carbon-carbon double bond into an
enol which tautomerizes to the carbonyl compound. It is a conceptually attractive approach, which compares favorably with the more conventional sequential two-step oxidation and reduction reactions. Several issues were addressed during the search for optimal
reaction conditions and will be detailed in the lecture. It includes (a) the choice of the catalyst, (b) the impact of the highly electron-withdrawing CF<sub>3</sub> group: electronic, steric, and position effects, (c) the gain of mechanistic insights, and
(d) the stereocontrol of the newly created stereogenic centre.<sup>[3]</sup></span><span lang="EN-US" style="font-size:12.0pt;line-height:115%;font-family:"Times","serif";mso-fareast-language:EN-US"><o:p></o:p></span></p>
<p class="MsoNormal" style="text-align:justify;text-autospace:none"><span lang="EN-US" style="font-size:12.0pt;line-height:115%;mso-fareast-language:EN-US">[</span><span lang="EN-US" style="mso-fareast-language:EN-US">1] (a) J.-A. Ma, D. Cahard,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Chem. Rev.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2008,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">108,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">PR1–PR43. (b) J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Chem. Rev.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2011,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">111,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">455–529.<o:p></o:p></span></p>
<p class="MsoNormal" style="text-align:justify;text-autospace:none"><span lang="EN-US" style="mso-fareast-language:EN-US">[2] (a) R. Uma, C. Crévisy, R. Grée,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Chem. Rev.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2003,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">103,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">27–51. (b) L. Mantilli, C. Mazet,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Chem. Lett.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2011,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">40,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">341–344.</span><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US"><o:p></o:p></span></p>
<p class="MsoNormal" style="text-align:justify;text-autospace:none"><span lang="EN-US" style="mso-fareast-language:EN-US">[3] (a) V. Bizet, X. Pannecoucke, J.L. Renaud, D. Cahard,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Angew. Chem. Int. Ed.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2012,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">51,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">6467–6470. (b) D. Cahard, V. Bizet, X. Dai, S. Gaillard, J.L. Renaud,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">J. Fluorine Chem.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2013,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">155,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">78–82. (c) V. Bizet, X. Pannecoucke, J.L. Renaud, D. Cahard,
</span><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">Adv. Synth. Catal.
</span></i><b><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">2014,
</span></b><i><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US">355,
</span></i><span lang="EN-US" style="mso-fareast-language:EN-US">1394–1402.</span><span lang="EN-US" style="font-family:"Times","serif";mso-fareast-language:EN-US"><o:p></o:p></span></p>
<p class="EndNoteBibliography" style="margin-bottom:0cm;margin-bottom:.0001pt"><span lang="EN-US" style="font-size:8.0pt;font-family:"Verdana","sans-serif""><o:p> </o:p></span></p>
<p class="MsoNormal" align="center" style="text-align:center;line-height:150%"><b><span lang="EN-US" style="font-size:14.0pt;line-height:150%;font-family:"Verdana","sans-serif"">Vljudno vabljeni! / Kindly invited!<o:p></o:p></span></b></p>
<p class="MsoNormal"><span style="font-size:11.0pt;line-height:115%;font-family:"Calibri","sans-serif";color:#1F497D"><o:p> </o:p></span></p>
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