Iridium-catalyzed dehydrogenation of alcohols
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1 Research Collection Doctoral Thesis idium-catalyzed dehydrogenation of alcohols Author(s): Tewes, Friederike Publication Date: 2009 Permanent Link: Rights / License: In Copyright - on-commercial Use Permitted This page was generated automatically upon download from the ET Zurich Research Collection. For more information please consult the Terms of use. ET Library
2 Dissertation ET o idium- Catalyzed Dehydrogenation of Alcohols A Dissertation Submitted to the ET Zürich For the Degree of Doctor of Science Presented by Friederike Tewes Dipl. Chem., Phillips University Marburg Born 11 th ovember 1980 Citizen of Germany Accepted on the Recommendation of Prof. Dr.. Grützmacher, examiner Prof. Dr. P.S. Pregosin, co- examiner Zürich 2009
3 Abstract Aldehydes are valuable synthetic intermediates, commonly prepared by the dehydrogenation of primary alcohols. Due to the increasing structural complexity of target molecules, the development of catalysts able to chemoselectively oxidize primary hydroxyl groups in polyols is a key challenge. In an earlier work, the chemoselective dehydrogenation of primary alcohols based on the homogeneous amino- olefin catalyst [(trop 2 DAC)] (trop 2 DAC =,- bis(5- - dibenzo[a,d]cycloheptene- 5- yl)- 1,2- diamino- cyclohexane) was explored. [1-3] The mechanism for this catalysis, however, was speculative and its scope limited to substrates with insensitive functional groups. This new work offers a deeper insight into the mechanism, including the successful isolation and characterization of the reactive intermediates of the catalytic cycle by MR and EPR spectroscopy. Furthermore, a 2 nd generation catalyst is introduced, which exhibits low catalyst loading and higher reaction rates under milder conditions. This new catalyst improves the functional group tolerance of the system and enlarges its scope to include primary alcohols with more sensitive and therefore more challenging functional groups. The mechanistic studies revealed that [(trop 2 DAC)] and the amino- olefin complexes newly synthesized in this work behave non- innocently under catalytic conditions and are only catalyst precursors: the true catalytically active species are the corresponding diazadiene- olefin complexes formed by oxidative dehydrogenation prior to catalysis (Scheme I). During the assessment of diazadiene complexes and co- oxidants, the highest catalytic activity was observed using [(trop 2 DAD)] (trop 2 DAD =,- bis(5- - dibenzo[a,d]cycloheptene- 5- yl)- 1,4- diazabuta- 1,3- diene) as the catalyst in combination with p- benzoquinone. Under mild, almost base free reaction conditions and low catalyst loadings (0.01 mol%), a wide range of primary aliphatic, benzylic, allylic alcohols were oxidized to the corresponding aldehydes. Aside from unactivated alcohols, the oxidation of naturally occurring alcohols such as lavandulol, geraniol and even a partially protected carbohydrate was possible. The most remarkable aspect of the catalytic system is its high group tolerance and selectivity, e.g. despite the unprotected secondary hydroxy group, 1,3- butandiol was selectively oxidized to 3- hydroxybutanal. The investigation of the catalytic cycle showed that the diazadiene ligand behaves as a cooperative ligand, as it actively contributes to the bond activation and is reversibly reduced and oxidized. Upon reaction with alcohols, [(trop 2 DAD)] was reduced to the mono(imino)mono(amino) complex [(trop 2 MIMA)] under formation of the aldehyde. In the last step of the catalytic cycle, II
4 [(trop 2 MIMA)] was reoxidized by p- benzoquinone to regenerate the diazadiene complex. Based on these results, the following catalytic cycle was proposed (Scheme I). Amino- lefin Complex - 4e [(trop 2 DAD)] [(trop 2 MIMA)] Scheme I: Proposed simplified mechanism for the dehydrogenation of alcohols with amino- olefin complexes. The chemoselective dehydrogenation of alcohols with [(trop 2 DAD)] is an attractive preparative method; in particular, as it reduces the need for a sophisticated group protection strategy. III
5 Zusammenfassung Aldehyde sind wichtige Zwischenprodukte in der organischen Synthese und werden üblicherweise durch xidation der entsprechenden Alkohole hergestellt. Aufgrund immer komplexeren Zielmoleküle, ist die Entwicklung neuer Katalysatoren, die in Polyolen selektiv die primäre ydroxylgruppen zu Aldehyden oxidieren eine der derzeitigen erausforderungen. Mit dem homogenen Amino- lefin Katalysator [(trop 2 DAC)] (trop 2 DAC =,- bis(5- - dibenzo[a,d]cyclohepten- 5- yl)- 1,2- diamino- cyclohexan) konnten gute Ergebnisse für die chemoselektive Dehydrierung von primären Alkoholen erzielt werden. [1-3] Der Anwendungsbereich war jedoch auf Substrate mit unempfindlichen funktionellen Gruppen beschränkt und über den Mechanismus konnte bisher nur spekuliert werden. Aufgrund der erfolgreichen Isolierung der Zwischenprodukte und deren Charakterisierung per MR- und EPR Spektroskopie, konnte in dieser Arbeit ein tiefer Einblick in den Katalysezyklus erhalten werden. Ausgehend von diesen Erkenntnissen, wurde ein Katalysator der zweiten Generation entwickelt, welcher sich durch mildere Reaktionsbedingungen, schnellere Reaktionsgeschwindigkeiten und eine höhere Toleranz gegenüber funktionellen Gruppen auszeichnet. Die mechanistischen Untersuchungen haben gezeigt, dass [(trop 2 DAC)] und die im Zuge dieser Doktorarbeit hergestellten Amino- lefin Komplexe nur Katalysator- Vorläufer sind. Unter katalytischen Bedingungen verhalten sie sich non- innocent und wandeln sich durch oxidative Dehydrierung in die katalytisch aktiven Diazadien- lefin Komplexe um (Schema II). Von den untersuchten Diazadien- lefin Komplexen und Co- xidationsmitteln wurde die besten Ergebnisse mit [(trop 2 DAD)] (trop 2 DAD =,- bis(5- - dibenzo[a,d]cyclohepten- 5- yl)- 1,4- diazabuta- 1,3- dien) und p- Benzoquinon erzielt. Unter milden, fast basenfreien Reaktionsbedingungen (0.01 mol%) und mit geringen Katalysatormengen (0.01 mol%), konnten die verschiedensten primären aliphatischen, benzylischen und allylischen Alkohole zu den entsprechenden Aldehyden umgesetzt werden. eben der xidation von unaktivierten Alkoholen war auch die xidation von natürlich vorkommenden Alkoholen wie Lavandulol, Geraniol und teilweise geschützten Kohlenhydraten möglich. Die Methode zeichnet sich vor allem durch die hohe Toleranz gegenüber verschiedenen funktionellen Gruppen und die gleichzeitiger Selektivität der xidation von primären ydroxylgruppen aus z.b. konnte 1,3- Butandiol trotz der ungeschützten sekundären ydroxylgruppe ausschließlich zu 3- ydroxybutanal dehydriert werden. Ausgehend vom Diazadien- lefin Katalysator [(trop 2 DAD)] wurde der Mechanismus des Katalysezykluses für die Dehydrierung von Alkoholen eingehend untersucht. Es konnte gezeigt werden, dass es sich bei dem Diazadien- lefin Liganden um einen kooperativen Liganden handelt, der während IV
6 der Katalyse aktiv an der Bindungsaktivierung beteiligt ist und reversibel reduziert und oxidiert wird. Durch die Reaktion mit Alkoholen wird [(trop 2 DAD)] unter Bildung des entsprechenden Aldehyds zum mono(imino)mono(amino) Komplex [(trop 2 MIMA)] reduziert. Im nächsten Schritt schließt sich der Katalyse- Zyklus durch die Reoxidation mit p- Benzoquinon zum Ausgangskomplex (Schema II). Amino- lefin Komplex - 4e [(trop 2 DAD)] [(trop 2 MIMA)] Schema II: Angenommener Reaktionsmechanismus der katalytischen Dehydrierung von Alkoholen mit Amino- lefin Komplexen. Insgesamt, ist mit dem [(trop 2 DAD)]- System eine attraktive, universelle Methode zur Dehydrierung von Alkoholen gelungen, insbesondere da auf die Verwendung von Schutzgruppen weitgehend verzichtet werden kann. V
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