Rhodium and Iridium Coordinated Aminyl Radicals: Synthesis and Catalytic Applications
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1 Dissertation ETH No Rhodium and Iridium Coordinated Aminyl Radicals: Synthesis and Catalytic Applications A dissertation submitted to the SWISS FEDERAL INSTITUTE OF TECHNOLOGY ZÜRICH for the degree of DOCTOR OF NATURAL SCIENCES presented by Nicola Donati Dipl, Chem. ETH born 20. August 1977 citizen oflavizzara (TI) accepted on the recommendation of Prof. Dr. H. Grützmacher. examiner Prof. Dr. A. Togni, co-examiner Zürich, 2007
2 Summary The first part of this work describes the synthesis of aminyl radicals that are stabilized through coordination to a rhodiumn) and iridiumü) metal center. For this purpose, the Iigand trop-nll (trop = 5H-dibenzo[a,d]cyc1ohepten-5-yl) is reacted with appropriate rhodium and iridium precursors and phenanthroline or its derivatives to pentacoordinated, trigonal bipyramidal complexes. The radical complexes are obtained by deprotonation and subsequent oxidation of the tropamine ligand and were characterized by a variety of analyticai methods. It is thereby found that the radicais are nitrogen-centered and are capable of hydrogenabstraction from different substrates. While rhodium aminyl radicals like 11 are storable for a virtually unlimited time, the iridium complex 17 is particularly reactive; however, its characterization by EPR spectroscopy succeeds at Iow temperature or in the presence of an excess of an electrolyte. Furthermore, the synthesis of the new ligands for the preparation ofcarbon-centered radicals is presented. 11: M = Rh(T) 17:M=Ir(T) 21: R= OH 22: R= =0 23: R= OAc 24: R= Cl The synthesis of the rhodium complexes is prescnted in the second part of the work. The complexes still contain the trop-nll ligand but a chiral center is introduced by using cysteine and methionine, Two new ligands which are derived from phenylalanine (29) or methionine (29) are presented together with the corresponding rhodium complexes. Thereby, the basics for the research ofchiral aminyl radicais is provided. III
3 26 : R = H, R' = H, TI = 1 27 : R = l.p., R' = CHzCB3, TI = 1 28: R = CH 3, R' = CH 3, TI = The third part of the thesis presents the catalytic oxidation of primary alcohols to the corresponding aldehydes using iridium stabilized aminyl radicals. The synthesis of the catalyst precursors and possible radical species are discussed. The catalytic reactivity is identical to the selective oxidation ofprimary alcohols in the enzyme galactose oxidase. NH ~ \,NH --.; ~I,I/' ~ r"" / -: \ "~I', \ \ \ 1+ o \\ F O:::S--J-F /. \ o F [Irttrop-dach-lHj] 40 [K(THF)x][Ir(tropzdach-2H)] 41 [Irttrop-dach)]OTf39 IV
4 Zusammenfassung Der erste Teil der vorliegenden Arbeit beschreibt die Synthese von Aminylradikalen, die durch Koordination an Rhodium(J) und Iridiumü) stabilisiert werden. Dazu wird der Ligand trop-nl-l (trop "" 5H-dibenzo[a,d]cyclohepten-5~yl) mit entsprechenden Rhodium- und Iridium-Vorläufern und Phenanthrolin oder dessen Derivate zu pentakoordinierten, trigonal bipyramidalen Komplexen umgesetzt. Durch Deprotonierung und nachfolgender Oxidation des trop-aminliganden erhält man die Radikalkomplexe, die durch diverse Analyseverfahren charakterisiert und auf ihre Reaktivität untersucht werden konnten. Dabei zeigt sich, dass es sich jeweils um stickstoffzentrierte Radikale handelt, die in der Lage sind, Wasserstoffradikale von verschiedenen Substraten zu abstrahieren. Während die Rhodium Aminylradikale, z.b. 11, praktisch unbegrenzt lagerfähig sind, ist der Iridium-Komplex 17 besonders reaktiv - bei tiefen Temperaturen bzw. in Anwesenheit eines Überschusses an Elektrolyten gelingt jedoch die Analyse mittels ESR-Spektroskopie. Weiterhin wird die Synthese der neuen Liganden für die Herstellung kohlenstoff-zentrierter Radikale vorgestellt. 11: M = Rh(l) 17: M = Ir(l) 21: R= OH 22: R= =0 23: R= OAc 24: R= CI Im zweiten Teil der Arbeit wird die Synthese der Rhodiumkomplexe aufgezeigt, die weiterhin auf dem dreizähnigen Liganden trop-nl] aufbauen, jedoch durch die Einführung von Cystein bzw. Methionin als Liganden ein Chiralitätszentrum enthalten. Weiterhin wird die Synthese zweier neuer Liganden vorgestellt, die sich von Phenylalanin (29) von Methionin (34) ableiten und zu den entsprechenden Rhodiumkomplexen führen. Dadurch wird der Grundstein für die Erforschung von chiralen Aminylradikalen gelegt. V
5 26 : R = H, R' = H, n = 1 27 : R = l.p., R' = CH 2CH3, n = 1 28 : R = CH 3, R' = CH 3, n = Der dritte Teil dieser Dissertation stellt die katalytische Oxidation von primären Alkoholen zu den entsprechenden Aldehyden mittels Iridium-stabilisierter Aminylradikale vor. Die Synthese der Katalysatorvorläufer und die möglichen Radikalspezies werden besprochen. Die katalytische Reaktivität gleicht der im Enzym Galaktose Oxidase beobachteten selektiven Oxidation von primären Alkoholen zu Aldehyden. o \\ F O===S---l-F 1- \ o F [Irrtropjdach-lHj] 40 [K(THF)x][Ir(trop2dach-2H)] 41 [Ir(trop2dach)]OTf39 VI
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