Selective hydrogen transfer reactions from alcohols to ketones promoted by rhodium complexes with 1,10-phenanthroline and related ligands |
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| Institution: | 1. Institute of Technical Science of SASA, 11000, Belgrade, Serbia;2. Faculty of Mechanical Engineering, University of Belgrade, 11000, Belgrade, Serbia;3. Faculty of Electronic Engineering, University of Nis, 18000, Nis, Serbia;4. CEITEC BUT, Brno University of Technology, 61600, Brno, Czechia |
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| Abstract: | Substituted cyclohexanones are effectively reduced to the corresponding alcohols using propan-2-ol as hydrogen source and Rh(I) complexes with 1,10-phenanthroline (phen) and substituted derivatives as catalyst precursors.Rh(I) derivatives with phen, 4,7-Ph2phen and 4,7-Mc2phen (chel/Rh ⩾ 2) promote the preferential formation of the axial alcohol (substrate = 4-t-butylcyclohexanone), while the 4,7-(MeO)2phen derivative gives in higher yield the equatorial isomer. Hindered substrates such as 2-methylcyclohexanone and 3,3,5-Me3cyclohexanone are reduced to the corresponding axial alcohol with a selectivity ⩾ 98% (chel = 4,7-Me2phen). |
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