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Homogeneous catalysis and mechanistic studies

The transition of chemical production to processes that are environmentally benign and sustainable is a big challenge for our society and for chemical research. Homogeneous catalysis can make a substantial contribution by developing processes that convert simple substrates into valuable products without using synthetic reagents in stoichiometric amounts or large amounts of energy. The development of such processes is the prime goal of our research group.

 

 

 

 

Martin Klußmann

PD Dr. Martin Klußmann

2011
Habilitation at the University of Cologne
since 2007
Group leader at the MPI für Kohlenforschung, associated with the group of Prof. Benjamin List and the University of Cologne
2004-2006
Postdoctoral research with Prof. Donna G. Blackmond at Imperial College London
2000-2004
PhD with Prof. Michael Reggelin at the TU Darmstadt.
1993–2000
Undergraduate studies at Johannes-Gutenberg-Universität Mainz, Friedrich-Schiller-Universität Jena and at the University of North Carolina at Chapel Hill, USA
2014
Award of Angewandte Chemie for frequent and competent reviews in 2013
2013
Award of Angewandte Chemie for frequent and competent reviews in 2012
2012
Heisenberg scholarship of the DFG
1993
Book prize of the Fonds der Chemischen Industrie
2008
Thieme Journal Award
2009
Global Young Faculty Member
2014

36). M. Scott, A. Sud, E. Boess, M. Klussmann,*:
Reaction Progress Kinetic Analysis of a Copper-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline.
J. Org. Chem. 2014, Article ASAP.

35.) N. Gulzar, M. Klussmann*:
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-Catalyzed C-H Functionalization via Intermediate Peroxides.
J. Vis. Exp. 2014, 88, e51504.

34.) N. Gulzar, B. Schweitzer-Chaput, M. Klussmann*:
Oxidative coupling reactions for the functionalisation of C-H bonds using oxygen.
Catal. Sci. Technol.
2014, 4, 2778-2796.

33.) B. Schweitzer-Chaput, J. Demaerel, H. Engler, M. Klussmann*:
Acid Catalysed Oxidative Radical Addition of Ketones to Olefins.
Angew. Chem. Int. Ed. 2014, 53, 8737-8740.

Säurekatalysierte oxidative Radikaladdition von Ketonen an Olefine.
Angew. Chem. 2014, 126, 8882-8885.

2013
32.) B. Schweitzer-Chaput, A. Sud, Á. Pinter, S. Dehn, P. Schulze, M. Klussmann*:
Synergistic effect of ketone and hydro(gen) peroxide in Brønsted acid catalyzed oxidative coupling reactions.
Angew. Chem. Int. Ed. 2013, 52, 13228-13232.

Synergistischer Effekt von Keton und Hydroperoxid in Brønsted-Säure-katalysierten oxidativen Kupplungen.
Angew. Chem. 2013, 125, 13470-13474.
 
31.) N. Gulzar, M. Klussmann*:
Aerobic C-H Amination of Tetrahydrocarbazole Derivatives via Photochemically Generated Hydroperoxides.
Org. Biomol. Chem. 2013.
 
30.) K. M. Jones, T. Hillringhaus, M. Klussmann*:
A Singlet Oxygen Approach to Oxaspirocycles.
Tetrahedron Lett. 2013, 54, 3294–3297.
 
29.) B. Schweitzer-Chaput, M. Klussmann*:                                             
Brønsted acid-catalyzed C-H Functionalisation of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides.
Eur. J. Org. Chem. 2013, 4, 666-671.
2012
28.) M. Klussmann:
Chemical Models for the Origin of Biological Homochirality.
In Genesis - In The Beginning: Precursors of Life, Chemical Models and Early Biological Evolution. Cellular Origin, Life in Extreme Habitats and Astrobiology series, Vol. 22 (Ed.: J. Seckbach), Springer, Berlin, 2012, 491-507.

27.) E. Böß, C. Schmitz, M. Klussmann*:
A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyl Tetrahydroisoquinoline.
J. Am. Chem. Soc. 2012, 134 (11), 5317-5325.

26.) M. Klussmann:
Mechanism in Organocatalysis.
In Science of Synthesis: Asymmetric Organocatalysis, Vol. 2 (Eds.: B. List, K. Maruoka), Thieme, Stuttgart, 2012, 633-671.

25.) Á. Pintér, M. Klussmann*:
Sulfonic Acid Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen.
Adv. Synth. Catal. 2012, 354, 701-711.

24.) K. M. Jones, M. Klussmann*:
Oxidative Coupling of Tertiary Amines: Scope, Mechanism and Challenges.
Synlett 2012, 23, 159-162.

23.) K. M. Jones, P. Karier, M. Klussmann*:
N-Alkyl Tetrahydroisoquinolines via V-Catalyzed Oxidative Coupling.
ChemCatChem 2012, 4, 51-54.
2011

22.) E. Böß, D. Sureshkumar, A. Sud, C. Wirtz, C. Farès, M. Klussmann*:
Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol as a Solvent.
J. Am. Chem. Soc. 2011, 133 (21), 8106-8109.

21.) E. Böß, T. Hillringhaus, J. Nitsch, M. Klussmann*:
Lewis-Acid Catalysed One Pot Synthesis of Substituted Xanthenes.
Org. Biomol. Chem. 2011, 9, 1744-1748.

20.) M. Klussmann*, D. Sureshkumar:
Catalytic Oxidative Coupling Reactions for the Formation of C–C Bonds Without Carbon-Metal Intermediates.
Synthesis 2011, 3, 353-369.

2010

19.) M. Klussmann*, L. Ratjen, S. Hoffmann, V. Wakchaure, R. Goddard, B. List*:
Synthesis of TRIP and Analysis of Phosphate Salt Impurities.
Synlett 2010, 14, 2189-2192.

18.) Á. Pintér, A. Sud, D. Sureshkumar, M. Klussmann*:
Autoxidative Carbon-Carbon Bond Formation from Carbon-Hydrogen Bonds.
Angew. Chem. Int. Ed. 2010, 49, 5004-5007.

Autoxidative Bildung von Kohlenstoff-Kohlenstoff-Bindungen aus Kohlenstoff-Wasserstoff-Bindungen.
Angew. Chem. 2010, 122, 5124-5128.

2009

17.) M. Klussmann*, D. G. Blackmond:
Origin of Homochirality.
In Chemical Evolution II: From the Origins of Life to Modern Society (Eds.: L. Zaikowski, J. M. Friedrich, S. R. Seidel), American Chemical Society, Washington D.C., 2009, 33-145.

16.) Martin Klussmann:
Asymmetric Reductive Amination by Combined Brønsted-Acid and Transition Metal Catalysis.
Angew. Chem. Int. Ed. 2009, 48, 7124-7125.

Asymmetrische reduktive Aminierung durch kombinierte Brønsted-Säure- und Übergangsmetallkatalyse.
Angew. Chem. 2009, 121, 7260-7261. 

15.) D. Sureshkumar, A. Sud, M. Klussmann*:
Thieme Chemistry Journal Awardees - Where Are They Now? Aerobic Oxidative Coupling of Tertiary Amines with Silyl Enolates and Ketene Acetals.
Synlett 2009, 1558-1561. 

14.) Abhishek Sud, Devarajulu Sureshkumar, Martin Klussmann*:
Oxidative coupling of amines and ketones by combined vanadium- and organocatalysis.
Chem. Commun. 2009, 21, 3169-3171. 

2007

13.) D.G. Blackmond*, Martin Klussmann:
Spoilt for Choice: Assessing Phase Behaviour Models for the Evolution of Homochirality.
Chem. Commun. 2007, 39, 3990-3996.

12.) M. Klussmann, T. Izumi, A.J.P. White, A. Armstrong, D.G. Blackmond*:
The Emergence of Solution-Phase Homochirality via Crystal Engineering of Amino Acids.
J. Am. Chem. Soc. 2007, 129, 7657-7660.

11.) D. G. Blackmond*, M. Klussmann:
Investigating the Evolution of Biomolecular Homochirality.
AIChE J. 2007, 53, 2-8.

2006

10.) M. Klussmann,* A. J. P. White, Alan Armstrong, D.G. Blackmond*:
Rationalization and Prediction of Solution Enantiomeric Excess in Ternary Phase Systems.
Angew. Chem. Int. Ed. 2006, 45, 7985-7989.
Angew. Chem. 2006, 118 , 8153-8157. (Hot Paper)

9.) M. Klussmann, S. P. Mathew, H. Iwamura, D. H. Wells jr., A. Armstrong, D. G.
Blackmond*:
Kinetic Rationalization of Nonlinear Effects in Proline-Mediated Reactions.
Angew. Chem. Int. Ed. 2006, 45, 7989-7992.
Angew. Chem. 2006, 118, 8157-8160.

8.) S. P. Mathew, M. Klussmann, H. Iwamura, D. H. Wells jr., A. Armstrong, D. G.
Blackmond*:
A Mechanistic Rationalization of Unusual Kinetic Behavior in Proline-Mediated
Reactions.
Chem. Commun. 2006, 41, 4291-4293. 

7.) M. Klussmann, H. Iwamura, S. P. Mathew, D. H. Wells jr., U. Pandya, A. Armstrong,
D. G. Blackmond*:
Thermodynamic control of asymmetric amplification in amino acid catalysis.
Nature 2006, 441, 621-623.

6.) J. S. Mathew, M. Klussmann, F. Valera, A. Futran, E. A. C. Emanuelsson, D. G. Blackmond*:
Mechanistic Studies of Pd-Catalyzed ArX Coupling Reactions Informed by Reaction Progress Kinetic Analysis.
J. Org. Chem. 2006, 71, 4711-4722.

2000-2004

5.) H. Iwamura, D. H. Wells jr., S. P. Mathew, M. Klussmann, A. Armstrong, D. G.
Blackmond*:
Probing the Active Catalyst in Product-Accelerated Proline-Mediated Reactions.
J. Am. Chem. Soc. 2004, 126, 16312-16313.

4.) M. Reggelin* S. Doerr, M. Klussmann, M. Schultz, M. Holbach:
Helically Chiral Polymers: A New Class of Ligands for Asymmetric Catalysis.
Proc. Natl. Acad. Sci. USA 2004, 101, 5461-5466. 

3.) S. Dörr, M. Klussmann, G. Wittmann:
Purification device, in particular for NMR tubes.
Patent-Nr. 2003-10320774, 2004, Technische Universität Darmstadt, Deutschland.

2.) H. Keutel*, D. Seidel, M. Klussmann, H. Goerls
An Unusual Metal-Mediated Formation of an Asymmetrical Carboxylate-Bridged Dinuclear Copper(II) Complex.
Inorg. Chem. 2000, 39, 1608-1610.

1.) M. Brauer, M. Kunert, E. Dinjus, M. Klussmann, M. Döring, H. Görls, E. Anders*:
Evaluation of the accuracy of PM3, AM1, and MNDO/d as applied to zinc compounds.
J. Mol. Struct. (Theochem) 2000, 505, 289-301.

 

DFG
Alexander von Humboldt-Stiftung

Fonds der Chemischen Industrie

2013 to date

Lecture and seminar "Fortgeschrittene Organische Chemie" for the bachelor degree course, University of Cologne

2008 to date

Lecture, seminar and pracitcal course in organic chemistry "Kalorimetrie und Kinetik", University of Cologne

October 2014

Anda and Sophia from Greece join the group for two months, funded by the ERASMUS-programme – welcome!

September 2014

A kinetic study on the reaction mechanism of the Cu-catalyzed oxidative coupling reaction with amines (N-phenyltetrahydroisoquinoline) appears online in J. Org. Chem. (J. Org. Chem., 2014, Article ASAP).

July 2014

Bertrand and Martin present research results at the EUCHEM Conference on Organic Free Radicals in Prague (http://www.uochb.cz/web/structure/1259.html).

June 2014

Bertrand finishes his PhD at the University of Cologne with grade 0,7 (magna cum laude, very good).

Our paper on the acid catalyzed oxidative addition of ketones to olefins (publicaton 33) is highlighted in SYNFACTS (Synfacts 2014, 10(7), 0758).

Research Topics

Oxidative Coupling Reactions
Oxidative Coupling Reactions

Oxidative Coupling Reactions

The activation of C-H bonds is an important goal in chemical research. The direct substitution of hydrogen in C-H bonds by a desired fragment creates interesting synthetic alternatives to the more common multi-step approach of first introducing reactive functional groups. Instead, only one step is needed and very simple substrates can be used, as C-H bonds are ubiquitous in organic compounds. Oxidative coupling reactions can achieve such transformations by utilizing an oxidant and a catalyst (reviews: see Ref. 20, 24 & 34).

Catalysis in organic synthesis
Catalysis in organic synthesis

Catalysis in organic synthesis

We are also developing other methods for direct and atom economic organic syntheses, for example to access starting materials for our projects or to apply strategies that were inspired by our mechanistic studies.

 

Mechanistic Studies
Mechanistic Studies

Mechanistic Studies

We are highly interested in investigating the mechanism of organic reactions. We study reactions developed in our own group, but also others and we are always interested in collaborations with other research groups. We use a variety of techniques, including synthetic (e.g. see ref. 27 and 32), spectroscopic (e.g. see NMR studies of intermediates in ref. 22 and 27) and kinetic studies (see ref. 32 and 36). To obtain kinetic data, we use NMR spectroscopy or reaction calorimetry. We like to evaluate the data by Donna Blackmond’s method of Reaction Progress Kinetic Analysis (see ref. 36 and 6).

 

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  •  Esther Böß

    Böß, Esther

    +49(0)208/306-2435

    boess((atsign))kofo.mpg.de

  •  Alexandra-Eleni Bosnidou

    Bosnidou, Alexandra-Eleni

    +49(0)208/306-2435

    bosnidou((atsign))kofo.mpg.de

  •  Joachim Demaerel

    Demaerel, Joachim

  •  Naeem Gulzar

    Gulzar, Naeem

    +49(0)208/306-2435

    gulzar((atsign))kofo.mpg.de

  •  Tim Hillringhaus

    Hillringhaus, Tim

  •  Andrei V. Iosub

    Iosub, Andrei V.

  • Dr. Kevin Mark Jones

    Dr. Jones, Kevin Mark

  •  Sofia Karanestora

    Karanestora, Sofia

    +49(0)208/306-2435

    karanestora((atsign))kofo.mpg.de

  •  Pol Karier

    Karier, Pol

  • PD Dr. Martin Klußmann

    PD Dr. Klußmann, Martin

    +49(0)208/306-2453

    klussmann((atsign))kofo.mpg.de

  •  Jan Kümmel

    Kümmel, Jan

  •  Jacqueline Nitsch

    Nitsch, Jacqueline

  •  Áron Pintér

    Pintér, Áron

  •  Corinna Schmitz

    Schmitz, Corinna

  • Dr. Bertrand Schweitzer-Chaput

    Dr. Schweitzer-Chaput, Bertrand

    +49(0)208/306-2435

    schweitz((atsign))kofo.mpg.de

  •  Abhishek Sud

    Sud, Abhishek

  •  Devarajulu Sureshkumar

    Sureshkumar, Devarajulu

  • Dr. Nobuhito Uemiya

    Dr. Uemiya, Nobuhito