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Coordination Chemistry and Asymmetric Homogeneous Catalysis

Research in our group is primarily directed toward the coordination chemistry of main group element in unusual oxidation states, the design of novel “frustrated Lewis pairs” and applications thereof to homogeneous catalysis and organic synthesis.

Manuel Alcarazo

Dr. Manuel Alcarazo

since 2008
Independent Junior Group Leader at the Max-Planck-Institut für Kohlenforschung
2005-2008
Postdoctoral research at the Max-Planck-Institut für Kohlenforschung (Prof. Dr. Alois Fürstner) on the “Design and applications of ylidic and bis-ylidic systems” and “Enantioselective protecting group-free total synthesis of ecklonialactone A and B”
2005
PhD from the Instituto de Investigaciones Químicas (CSIC) (Dr. José M. Lassaletta) on the “Synthesis and structure of new NHC-ligands”
2002
Master Degree from the University of Seville, Spain (Prof. Dr. Rosario Fernández) on the “Synthesis and applications of bis-hydrazones as ligands in asymmetric catalysis”
2000
Chemistry Degree from the University of Seville, Spain
1978
born in Alcalá de Guadaira, Spain
2013
Young Scientist Award from the Academy of Sciences of Göttingen
2013
ADUC Annual Prize for Habilitands 2012
2013
Science Award of the Industrie-Club Duesseldorf and the North Rhine-Westphalian Academy of Sciences, Humanities and the Arts
2013-2017
Lecturer's scholarship ("Dozentenstipendium") of the Chemical Industry Fund
2012
Sponsorship Award of Dr. Otto Roehm Commemoration Foundation
2011
European Research Council Starting Grant for his research “Activation of small molecules by organic frustrated Lewis pairs"
2011
Sigma-Aldrich-RSEQ Prize for Outstanding Emerging Researcher
2010
Thieme Journal Award 2010
2009
Young Scientist Award from the Academy of Sciences of Seville, Spain
2007
Best PhD Thesis in Chemistry, University of Seville, Spain
2005-2007
Post-Doctoral Fellowship of the Spanish Ministry of Education and Science
2005
Research Fellowship from the Spanish Council for Scientific Research (CSIC)
2001-2005
PhD Scholarship from the Spanish Ministry of Education and Science (Short stays at Aarhus, Denmark (Prof. K. A. Jørgensen) and Oxford, United Kingdom (Prof. J. M. Brown))
2001
Scholarship from the Spanish Agency of International Cooperation (Universidad Nacional Autónoma de México)
2000
Graduation Prize from the University of Seville, Spain
2000
Cooperation Scholarship with the Department of Organic Chemistry, University of Seville, Spain

 

Total Synthesis (I), TU Dortmund, WS 2009/2010

Principles in Organometallic Chemistry, TU Dortmund, SS 2010

Stereoselective Synthesis (I), TU Dortmund, WS 2010/2011

Stereoselective Synthesis (II), TU Dortmund, SS 2011

Total Synthesis (I), TU Dortmund, WS 2011/2012

Stereoselective Synthesis, Heinrich-Heine University Düsseldorf, SS 2012 (please find the slides here)

since 2014
Member of the Editorial Advisory Board of "Organometallics"
since 2009
Member of Global Young Faculty
since 2008
Group leader at the Max-Planck-Institut für Kohlenforschung
2014

51. "Bis- and Tris(pyrazolyl)borate/methane-Stabilized PIII-Centered Cations. L. Gu, G. Gopakumar, P. Gualco, W. Thiel, M. Alcarazo, Chem.–Eur. J. DOI: 10.1002/chem.201402636.

50. "Synthesis, Structure, and Applications of Pyridiniophosphines" H. Tinnermann, C. Wille, M. Alcarazo, Angew. Chem. Int. Ed. DOI: 10.1002/anie.201401073.

49. "ɑ-Cationic Phosphines: Synthesis and Applications" M. Alcarazo, Chem.–Eur. J. 2014, 20, 7868.

48. "Coordination Chemistry of Cyclopropenylidene-Stabilized Phosphenium Cations: Synthesis and Reactivity of Pd and Pt Complexes" Á. Kozma, T. Deden, J. Carreras, C. Wille, J. Petuškova, J. Rust, M. Alcarazo, Chem.–Eur. J. 2014, 20, 2208.

2013

   47. "Polycationic Ligands in Gold Catalysis: Synthesis and Applications of Extremely π-Acidic Catalysts" J. Carreras, G. Gopakumar, L. Gu, A. Gimeno, P. Linowski, J. Petuškova, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2013, 135, 18815.

   46. "Synthesis and reactivity of metal complexes with acyclic (amino)(ylide)carbene ligands" E. González-Fernández, J. Rust, M. Alcarazo, Angew. Chem. Int. Ed. 2013, 52, 11392.

   45. "Tuning the Lewis acidity of boranes in frustrated Lewis pair chemistry: implications for the hydrogenation of electron-poor alknes" J. A. Nicasio, S. Steinberg, B. Inés, M. Alcarazo, Chem.–Eur. J. 2013, 19, 11016.

   44. "Carbon-based frustrated Lewis pairs" S. Khan, M. Alcarazo, Top. Curr. Chem. 2013, 334, 157.

   43. "Synthesis, structure and reactivity of cyclopropenyl-1-ylidene stabilized S(II), Se(II) and Te(II) mono- and dications" Á. Kozma, J. Petuškova, C. W. Lehmann, M. Alcarazo, Chem. Commun. 2013, 49, 4145.

   42. "Stabilization of a two-coordinate [GeCl]+ cation by simultaneous σ and π donation from a monodentate carbodiphosphorane" S. Khan, G. Gopakumar, W. Thiel, M. Alcarazo, Angew. Chem. Int. Ed. 2013, 52, 5644.

   41. "Chiral heterobimetallic complexes of carbodiphosphoranes and phosphinidene–carbene adducts" M. Alcarazo, K. Radkowski, G. Mehler, R. Goddard, A. Fürstner, Chem. Commun. (Cambridge, U. K.) 2013, 49, 3140.

   40. "Synthesis and structure of carbene-stabilized N-centered cations [L2N]+, [L2NR]2+, [LNR3]2+ and [L3N]3+" Á. Kozma, G. Gopakumar, C. Farès, W. Thiel, M. Alcarazo, Chem.–Eur. J. 2013, 19, 3542.

2012

   39. "Metal-free hydrogenation of electron-poor allenes and alkenes" B. Inés, D. Palomas, S. Holle, S. Steinberg, J. A. Nicasio, M. Alcarazo, Angew. Chem. Int. Ed. 2012, 51, 12367.

   38. "Exploiting the π-acceptor properties of carbene-stabilized phosphorus centered trications [L3P]3+: applications in Pt(II) catalysis" J. Carreras, M. Patil, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2012, 134, 16753.

   37. "At the frontiers of knowledge in chemistry: the 47th Bürgenstock conference" O. García-Mancheño, M. Alcarazo, Angew. Chem. Int. Ed. 2012, 51, 8151.

   36. "Synthesis and reactivity of electron poor allenes: formation of completely organic frustrated Lewis pairs" D. Palomas, S. Holle, B. Inés, H. Bruns, R. Goddard, M. Alcarazo, Dalton Trans. 2012, 41, 9073.

   35. "Pyracenebis(imidazolylidene): a new Janus-type biscarbene and its coordination to rhodium and iridium" A. Prades, E. Peris, M. Alcarazo, Organometallics 2012, 31, 4623. 

   34. "Fullerenes as neutral carbon-based Lewis acids" J. Iglesias-Sigüenza, M. Alcarazo, Angew. Chem. Int. Ed. 2012, 51, 1523.

2011

    33. "Synthesis, structure, and reactivity of carbene-stabilized phosphorus(III)-centered trications [L3P]3+" J. Petuškova, M. Patil, S. Holle, C. W. Lehmann, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2011, 133, 20758.

    32. "Catalysis-based and protecting-group-free total syntheses of the marine oxylipins hybridalactone and the ecklonialactones A, B, and C" V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471.

    31. "Synthesis, structure, and reactivity of a dihydrido borenium cation" B. Inés, M. Patil, J. Carreras, R. Goddard, W. Thiel, M. Alcarazo, Angew. Chem. Int. Ed. 2011, 50, 8400.

    30. "Cyclopropenylylidene-stabilized diaryl and dialkyl phosphenium cations: applications in homogeneous gold catalysis" J. Petuškova, H. Bruns, M. Alcarazo, Angew. Chem. Int. Ed. 2011, 50, 3799.

    29. "On the metallic nature of carbon in allenes and heterocumulenes" M. Alcarazo, Dalton Trans. 2011, 40, 1839.

    28. "Metal complexes with carbene ligands stabilized by lateral enamines" M. Alcarazo, K. Radkowski, R. Goddard, A. Fürstner, Chem. Commun. 2011, 47, 776.

2010

    27. "Heterocyclic S–S bond cleavage by a purely carbogenic frustrated Lewis pair" B. Inés, S. Holle, R. Goddard, M. Alcarazo,  Angew. Chem. Int. Ed. 2010, 49, 8389.

    26. "A new class of singlet carbene ligands" M. Alcarazo, R. M. Suárez, R. Goddard, A. Fürstner, Chem.–Eur. J. 2010, 16, 9746.

    25. "Protecting-group-free and catalysis-based total synthesis of the ecklonialactones" V. Hickmann, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11042.

    24. "Exploring the reactivity of carbon (0)/borane-based frustrated Lewis pairs" M. Alcarazo, C. Gomez, S. Holle, R. Goddard, Angew. Chem. Int. Ed. 2010, 49, 5788 [Erratum: Angew. Chem. Int. Ed. 2010, 49, 5597].

    23. "Stereoselective synthesis of cationic heterobidentate C(NHC)/SR rhodium(I) complexes using stereodirecting N,N-dialkylmaino groups" A. Ros, M. Alcarazo, D. Monge, E. Álvarez, R. Fernández, J. M. Lassaletta, Tetrahedron: Asymmetry 2010, 21, 1557.

    22. "Synthesis and coordination properties of nitrogen(I)-based ligands" H. Bruns, M. Patil, J. Carreras, A. Vázquez, W. Thiel, R. Goddard, M. Alcarazo, Angew. Chem. Int. Ed. 2010, 49, 3680.

    21. "Steering the surprisingly modular π-acceptor properties of N-heterocyclic carbenes: Implications for gold catalysis" M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem. Int. Ed. 2010, 49, 2542.

2009

    20. "Synthesis, structure and properties of [1,2,4]triazolo[4,3-a]pyridin-3-ylidene rhodium and palladium complexes" J. Iglesias-Sigüenza, A. Ros, E. Díez, M. Alcarazo, E. Álvarez, R. Fernández, J. M. Lassaletta, Dalton Trans. 2009, 7113.

    19. "Tetrakis(dimethylamino)allene" A. Fürstner, M. Alcarazo, H. Krause, Org. Synth. 2009, 86, 298.

    18. "Coordination Chemistry at Carbon" M. Alcarazo, C. W. Lehmann, A. Anoop, W. Thiel, A. Fürstner, Nat. Chem. 2009, 1, 295.

2008

    17. "Stereoselective synthesis of Rh(I) 4-(dialkylamino)triazol-5-yledene complexes" A. Ros, M. Alcarazo, J. Iglesias-Sigüenza, E. Díez, E. Álvarez, R. Fernández, J. M. Lassaletta, Organometallics 2008, 27, 4555.

    16. "Carbenes stabilized by ylides: pushing the limits" A. Fürstner, M. Alcarazo, K. Radkowski , W. Lehmann,  Angew. Chem. Int. Ed. 2008, 47, 8302.

    15. "Coordination chemistry of ene-1,1-diamines and a prototype "carbodicarbene"" A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. Int. Ed. 2008, 47, 3210.

    14. "Preparation of a non-symmetrical imidazolium salt: 1-adamantyl-3-mesityl-4,5-dimethylimidazaloium tetrafluoroborate" A. Fürstner, M. Alcarazo, V. César, H. Krause, Org. Synth. 2008, 85, 34.

2007

    13. "Effective modulation of the donor properties of N-heterocyclic carbene ligands by "through-space" communication within a planar chiral scaffold" A. Fürstner, M. Alcarazo, H. Krause, C. W. Lehmann, J. Am. Chem. Soc. 2007, 129, 12676.

    12. "Enantioselective conjugate addition of N,N-dialkylhydrazones to α-hydroxy enones" D. Monge, E. Martín-Zamora, J. Vázquez, M. Alcarazo, E. Álvarez, R. Fernández, J. M. Lassaletta, Org. Lett. 2007, 9, 2867.

    11. "Imidazo[1,5-a]pyridin-3-ylidene/thioether mixed C/S ligands and complexes thereof" S. J. Roseblade, A. Ros, D. Monge, M. Alcarazo, E. Álvarez, J. M. Lassaletta, R. Fernández, Organometallics 2007, 26, 2570.

    10. "Isoquinolin-1-ylidenes as electronically tuneable ligands" S. Gómez-Bujedo, M. Alcarazo, C. Pichon, E. Álvarez, R. Fernández, J. M. Lassaletta, Chem. Commun. 2007, 1180.

2005-2006

    9. "Synthesis, structure and applications of N-dialkylamino-N’-alkylimidazol-2-ylidenes as a new type of NHC ligands" A. Ros, D. Monge, M. Alcarazo, E. Álvarez, J. M. Lassaletta, R. Fernández, Organometallics 2006, 25, 6039.

    8. "Convenient, scalable and flexible method for the preparation of imidazolium salts with previously inaccessible substitution patterns" A. Fürstner, M. Alcarazo, V. César, C. W. Lehmann, Chem. Commun. 2006, 2176.

    7. "Synthesis, structure and electronic properties of N-dialkylamino and N-alkoxy-1,2,4-triazol-3-ylidene ligands" M. Alcarazo, R. Fernández, E. Álvarez, J. M. Lassaletta, J. Organomet. Chem. 2005, 690, 5979.

    6. "Magnesium bis(monoperoxyphathalate) hexahydrate (MMPP)" M. Alcarazo Velasco, Synlett 2005, 1807.

    5. "Imidazo[1,5-a]pyridine: A versatile architecture for N-Heterocyclic carbenes" M. Alcarazo, S. J. Roseblade, A. R. Cowley, R. Fernández, J. M. Brown, J. M. Lassaletta, J. Am. Chem. Soc. 2005, 127, 3290.

2001-2004

    4. "1,3-Bis(N,N-dialkylamino)imidazolin-2-ylidenes: synthesis and reactivity of a new family of stable N-heterocyclic carbenes" M. Alcarazo, S. J. Roseblade, E. Alonso, R. Fernández, E. Alvarez, F. J. Lahoz, J. M. Lassaletta, J. Am. Chem. Soc. 2004, 126, 13242.

    3. "Glyoxal bis-hydrazones: a new family of nitrogen ligands for asymmetric catalysis" J. M. Lassaletta, M. Alcarazo, R. Fernández, Chem. Commun. 2004, 298.

    2. "Synthesis and spectroelectrochemical studies of mixed heteroleptic chelate complexes of ruthenium (II) with 1,8-bis(2-pyridyl)-3,6-dithiaoctane (pdto) and substituted 1,10-phenanthrolines" L. A. Ortiz-Frade, L. Ruiz-Ramírez, I. González, A. Marín-Becerra, M. Alcarazo, J. G. Alvarado-Rodriguez, R. Moreno-Esparza, Inorg. Chem. 2003, 42, 1825.

    1. "Synthesis of α-hydroxyhydrazones from aldehydes" R. Fernández, E. Martín-Zamora, C. Pareja, M. Alcarazo, J. Martín, J. M. Lassaletta, Synlett 2001, 1158.

 

Organometallic Chemistry (II), TU Dortmund, WS 2013/2014

Organometallic Chemistry (I), TU Dortmund, SS 2013

Stereoselective Synthesis, Heinrich-Heine University Düsseldorf, SS 2012

Total Synthesis (I), TU Dortmund, WS 2011/2012

Stereoselective Synthesis (II), TU Dortmund, SS 2011

Stereoselective Synthesis (I), TU Dortmund, WS 2010/2011

Principles in Organometallic Chemistry, TU Dortmund, SS 2010

Total Synthesis (I), TU Dortmund, WS 2009/2010

 

 

Research Topics

Cationic ligands: synthesis and applications of extreme π-acid catalysts

Cationic ligands: synthesis and applications of extreme π-acid catalysts

The goal of this project is the synthesis of extreme π-acceptor phosphines through the introduction of positively charged homo- or heteroaromatic substituents directly attached to the phosphorus atom. By exploiting this property, new Au and Pt catalysts have been developed that display a dramatically enhanced capacity to activate π-systems.
Very recently, we reported the synthesis of the first ever isolated carbene-stabilized P1-centered trication [L3P]3+ (L = 2,3-dialkylaminocyclopropenium) 1 by reaction of the 1-chloro-2,3-(dimethylamino) cyclopropenium salt 2 and P(SiMe3)3 (Scheme 1). Despite the three positive charges on the groups directly attached to the P atom, this compound can still serve as a ligand for π-acidic metals such as Pt. Thus, when 1 is treated with K2PtCl4 in acetonitrile, the bench stable complex 3 is formed. More interestingly, charge decomposition analysis of the metal-ligand interaction in 3 gave the surprising result that the total L→M σ-donation (0.31 e) is lower than the L→M π-back donation (0.43 e) into the very low-lying LUMO of 1, which must hence be regarded as the main interaction in 3. This unconventional situation in which the P-ligand removes net electron density from the metal suggests that compound 1 increases the natural π-acidity of Pt(II) centers. It should thus accelerate known reactions, or even permit new ones, in which either the coordination of the substrate or the nucleophilic attack to the activated substrate are the rate-determining steps.
Accordingly, we chose for our studies on ligand effects a series of phosphanes such as PPh3, P(OPh)3, P(C6F5)3 and precatalyst 3 in combination with a silver salt. As expected, both P(OPh)3 and P(C6F5)3 performed better than PPh3 in terms of reactivity (Scheme 2).
In addition, our synthetic program has already benefitted from these novel tools and natural products such as Orchinol, Ochrolide, Bulbophyllantrin and Epimedoicarisoside A have been prepared using our Pt and Au catalysts for the key hydroarylation step (Scheme 3).
 

Synthesis and applications of simultaneous σ- and π-donor ligands: C-M dative double bonds

Synthesis and applications of simultaneous σ- and π-donor ligands: C-M dative double bonds

In this area, our research has been strongly inspired by the theoretical work of Frenking about the nature of carbodiphosphorane 1 (Scheme 1). His studies revealed that in compound 1 and analogues the central carbon atom retains its four valence electrons that are thus all available for coordination. In fact, carbodiphosphoranes are known to react with two Lewis acids such as AuCl affording diaurated derivatives. However, their ability to donate their four electrons to the same electrophile in a simultaneous σ- and π-donation had not been described.
In this regard, we envisaged that the use carbodiphosphoranes may provide sufficient stabilization to attenuate the reactivity and allow the isolation of dihydrido borenium cations [L→BH2]+ (L = carbodiphosphorane), a series of compounds that cannot be isolated when classical σ-donating ligands are employed.
Our strategy is already producing some positive results with other low valent cations. Up to now we have been able to synthesize compound 4 which already depicts a σ- and π-dative bond between the central carbon atom and the GeCl moiety. Reaction with dimethylamino pyridine affords adduct 5 where the π interaction is not existing anymore.
 

 

Research Reports

 

Staff

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  • Dr. Ibrahim Abdellah

    Dr. Abdellah, Ibrahim

    Oct 12 – Sep 13 Post-doc

  • Dr. Manuel Alcarazo

    Dr. Alcarazo, Manuel

    +49(0)208/306-2428

    alcarazo((atsign))kofo.mpg.de

  • Dr. Isaac Alonso García

    Dr. Alonso García, Isaac

    +49(0)208/306-2473

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  • Dr. Javier Carreras

    Dr. Carreras, Javier

    Jan 11 – Feb 13 Post-doc

  •  Paolo Costa

    Costa, Paolo

    Dec 11 – Apr 12 PhD Student

  •  Tobias Deden

    Deden, Tobias

    Jan 13 – Aug 13 MSc Student

  • Dr. Jonathan Dube

    Dr. Dube, Jonathan

    +49(0)208/306-2474

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  •  Alejandro García Barrado

    García Barrado, Alejandro

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  •  Ana Maria Gimeno Cardells

    Gimeno Cardells, Ana Maria

    Jun 12 – Sep 12 Visiting PhD Student

  •  Elisa Gonzalez Fernández

    Gonzalez Fernández, Elisa

    +49(0)208/306-2475

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  •  Lianghu Gu

    Gu, Lianghu

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  • Dr. Pauline Gualco

    Dr. Gualco, Pauline

    May 12 – Apr 13 Post-doc

  • Dr. Estella Haldón Hermoso

    Dr. Haldón Hermoso, Estella

    +49(0)208/306-2473

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  •  Sigrid Holle

    Holle, Sigrid

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  • Dr. Francisco J. Iglesias Sigüenza

    Dr. Iglesias Sigüenza, Francisco J.

    Jul 11 - Jun 12 Post-doc

  • Dr. Blanca Ines Tejedor

    Dr. Ines Tejedor, Blanca

    Jan 10 – Dec 11 Post-doc; Jan 12 – Dec 12 Scientific Co-worker

  • Dr. Shabana Khan

    Dr. Khan, Shabana

    Oct 11 – Dec 12 Scientific Co-worker

  •  Betina Klein

    Klein, Betina

    Sep 09 – Jan 13 Trainee

  •  Ágnes Kozma

    Kozma, Ágnes

    +49(0)208/306-2475

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  •  Pawel Linowski

    Linowski, Pawel

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  •  Maria del Rocío  López Rodríguez

    López Rodríguez, Maria del Rocío

    +49(0)208/306-2427

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  •  Sergio Joaquin Alvarez Méndez

    Alvarez Méndez, Sergio Joaquin

    Aug 13 – Oct 13 Visiting PhD Student

  • Dr. Francisca María Martín Gálvez

    Dr. Martín Gálvez, Francisca María

    Feb 13 – Feb 14 post-doc

  •  Gerlinde Mehler

    Mehler, Gerlinde

    +49(0)208/306-2429

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  •  Juan Antonio Nicasio Collazo

    Nicasio Collazo, Juan Antonio

    May 12 – Apr 13 Visiting PhD Student

  •  Leo David Mwenya Nicholls

    Nicholls, Leo David Mwenya

    +49(0)208/306-2430

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  • Dr. David Palomas Dona

    Dr. Palomas Dona, David

    Mar 10 – Feb 12 Post-doc

  • Dr. Javier Peña Gonzalez

    Dr. Peña Gonzalez, Javier

    +49(0)208/306-2430

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  •  Jekaterina Petuškova

    Petuškova, Jekaterina

    Apr 09 – Mar 12 PhD Student

  •  Amparo Prades Ferrer

    Prades Ferrer, Amparo

    Sep 11 – Nov 11 Visiting PhD Student

  •  María del Carmen Pérez Aguilar

    Pérez Aguilar, María del Carmen

    May – Jul 14 Visiting PhD Student

  • Dr. Azhakar Ramachandran

    Dr. Ramachandran, Azhakar

    May 13 – May 14 Post-doc

  •  Angus Rocha Vogel

    Rocha Vogel, Angus

    +49(0)208/306-2474

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  •  Dominik Schauenburg

    Schauenburg, Dominik

    Jan 13 – Mar 13 BSc Student

  •  Sebastian Steinberg

    Steinberg, Sebastian

    +49(0)208/306-2475

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  • Dr. Garazi Talavera Urquijo

    Dr. Talavera Urquijo, Garazi

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  •  Hendrik Tinnermann

    Tinnermann, Hendrik

    +49(0)208/306-2475

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  •  Jens Truckenbrodt

    Truckenbrodt, Jens

    Jul 11 – Jan 12 Permanent Staff

  •  Christian Wille

    Wille, Christian

    +49(0)208/306-2473

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  • Dr. Alessandro Zanardi

    Dr. Zanardi, Alessandro

    Jan 13 – Apr 13 Post-doc; May 13 – Mar 14 Scientific Co-worker