Paul Knochel

Paul Knochel (born 15 November 1955) is a French chemist and a member of the French Academy of Sciences.

Biography

Paul Knochel was born in Strasbourg. He studied chemistry at the IUT (Institut Universitaire de Technologie) in Strasbourg, then at the ENSCS (École Nationale Supérieure de Chimie de Strasbourg). From 1979 to 1982, he completed his thesis entitled "Nitroallyl-halogenide und -ester als effiziente Verknüpfungsreagenzien" at ETH (Eidgenössische Technische Hochschule) Zurich (Switzerland) in Prof. Dieter Seebach's group. He then spent 4 years at the CNRS (Centre National de la Recherche Scientifique) at the Pierre et Marie Curie University in Paris in the group of Prof. Jean-François Normant. During this period, he studied carbozincation reactions using allylic reagents and prepared bimetallic compounds bearing two different metals (Lithium, Magnesium or Zinc) on the same carbon atom. He then joined Prof. Martin F. Semmelhack's laboratory for a post-doctoral fellowship during which he worked on the use of indoles-chromium complexes in organic synthesis. In 1987, he accepted a position as Assistant Professor in the Department of Chemistry at the University of Michigan at Ann Arbor (MI, USA) where he developed the first methods for the preparation of polyfunctional organometallic zinc species. In 1991, he was promoted to Professor at the same University before moving to Marburg (Germany) in 1992, where he was offered a position as Professor of Organic Chemistry in the Department of Chemistry at the Philips-Universität University. He continued his work on the chemistry of polyfunctional organozinciques and their use in asymmetric synthesis. In 1999, he was offered a position as Professor of Organic Chemistry at the University of Munich (Ludwig-Maximilians-Universität - LMU)[1][2] which he still holds in 2019. He has developed new methods for the preparation of polyfunctional organometallic species as well as numerous synthetic methods using organometallic reagents or catalysts.

Scientific work

Paul Knochel has developed a series of new methods for the preparation of polyfunctional organometallic species of zinc[3] and magnesium, but also many other metals such as copper, aluminium,[4] manganese, indium, iron, lanthanum and samarium. In addition, he highlighted the fact that lithium salts catalyse a significant number of organometallic reactions, including the oxidative addition of a metal such as magnesium,[5] zinc[6] 6, indium, manganese or aluminium to an organic halide. It has shown that the use of lithium derivatives (chloride, acetylacetonates or alcoholates)[7][8] catalyses the halogen-metal exchange in the preparation of organomagnesians[8] and organozinciques. In addition, it has synthesized a series of new cluttered metal bases derived from tetramethylpiperidine allowing C-H activations of aromatic and heterocyclic unsaturated systems.[9][10] He has also conducted research on a series of diastereoselective mixed coupling reactions catalyzed by palladium, iron, cobalt[11] and chromium. He has succeeded in considerably increasing the scope of these organic synthesis reactions through continuous flow chemistry.[12][13][14][15][16][17] It has also implemented a synthetic methodology for the preparation of lithians,[18][19][20] zinciques and organocuprates with high enantioselectivity and has demonstrated the usefulness of this method for preparing pheromones[18] containing up to five chiral centres. By using additives such as zinc or magnesium pivalate, it has been possible to prepare organozinciques with high stability against air and moisture.[15][21]

Honours and awards
  • Berthelot Medal of the French Academy of Sciences (Paris) 1992
  • IUPAC Thieme Prize 1994
  • ECS - European Chemical Society - Chiroscience Award for Creative European Chemistry 1995
  • Otto-Bayer Prize 1995
  • Leibniz Prize 1996
  • Merck Sharp & Dohme Research Award 2000/2001
  • V. Grignard Prize 2000
  • Dr. Paul Janssen Prize for Creativity in Organic Synthesis 2004
  • Cope Scholar Award of the American Chemical Society 2005
  • Lilly European Distinguished Lectureship Award 2007
  • Member of the French Academy of Sciences (Paris) 2007[22]
  • Member of the Bavarian Academy of Science 2008
  • Karl-Ziegler-Preis 2009
  • Member of the German Academy of Sciences Leopoldina 2009[23]
  • EROS (Encyclopedia of Reagents for Organic Synthesis) Best Reagent Award. 2011
  • Gold Nagoya Medal of Organic Chemistry 2012
  • Chevalier dans l'Ordre national du Mérite 2013[24]
  • Herbert C. Brown Award for Creative Research in Synthetic Methods 2014

References
  1. "LMU".
  2. "Département de chimie de LMU".
  3. Ellwart, M.; Knochel, P., « Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles », Angew. Chem. Int. Ed., 2015, 54, p. 10662-10665
  4. Bluemke, T.; Chen, Y.-H.; Peng, Z.; Knochel, P., « Preparation of functionalized organoaluminiums by direct insertion of aluminium to unsaturated halides », Nature Chem., 2010, 2, p. 313-318
  5. Krasovskiy, A.; Knochel, P., « A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides », Angew. Chem. Int. Ed., 2004, 43, p. 3333-3336
  6. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P., « Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides », Angew. Chem. Int. Ed., 2006, 45, p. 6040-6044
  7. Kneisel, F. F.; Dochnahl, M.; Knochel, P., « Nucleophilic Catalysis of the Iodine-Zinc Exchange Reaction: Preparation of Highly Functionalized Diaryl Zinc Compounds », Angew. Chem. Int. Ed., 2004, 43, p. 1017-1021
  8. Ziegler, D. S.; Karaghiosoff, K.; Knochel, P., « Generation of Aryl and Heteroaryl Magnesium Reagents in Toluene by Br/Mg or Cl/Mg Exchange », Angew. Chem. Int. Ed., 2018, 57, p. 6701-6704
  9. Makarov, I. S.; Brocklehurst, C. E.; Karaghiosoff, K.; Koch, G.; Knochel, P., « Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane », Angew. Chem. Int. Ed., 2017, 56, p. 12774-12777
  10. Haag, B.; Mosrin, M.; Hiriyakkanavar, I.; Malakhov, V.; Knochel, P., «  Regio- and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases», Angew. Chem. Int. Ed., 2011, 50, p. 9794-9824
  11. Chen, Y.-H.; Grassl, S.; Knochel, P., « Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates », Angew. Chem. Int. Ed., 2018, 57, p. 1108-1111
  12. Weidmann, N.; Ketels, M.; Knochel, P., « Sodiation of Arenes and Heteroarenes in Continuous Flow », Angew. Chem. Int. Ed., 2018, 57, p. 10748-10751
  13. Ganiek, M. A.; Becker, M. R.; Berionni, G.; Zipse, H.; Knochel, P., « Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation », Chem. Eur. J., 2017, 23, p. 10280-10284
  14. Becker, M. R.; Ganiek, M. A.; Knochel, P., « Practical and economic lithiations of functionalized arenes and heteroarenes using Cy2NLi in the presence of Mg, Zn or La halides in a continuous flow », Chem. Science, 2015, 6, p. 6649-6653
  15. Chen, Y.-H.; Ellwart, M.; Toupalas, G.; Ebe, Y.; Knochel, P., « Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability », Angew. Chem. Int. Ed., 2017, 56, p. 4612-4616
  16. Becker, M. R.; Knochel, P., « Practical Continuous-Flow Trapping Metalations of Functionalized Arenes and Heteroarenes Using TMPLi in the Presence of Mg, Zn, Cu, or La Halides », Angew. Chem. Int. Ed., 2015, 54, p. 12501-12505
  17. Stathakis, C. I.; Bernhardt, S.; Quint, V.; Knochel, P., « Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings », Angew. Chem. Int. Ed., 2012, 51, p. 9428-9432
  18. Morozova, V.; Skotnitzki, J.; Moriya, K.; Karaghiosoff, K.; Knochel, P., « Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper Reagents-Synthesis of (-)-Lardolure and Siphonarienal », Angew. Chem. Int. Ed., 2018, 57, p. 5516-5519
  19. Dagousset, G.; Moriya, K.; Mose, R.; Berionni, G.; Karaghiosoff, K.; Knochel, P., « Diastereoselective Synthesis of Open-Chain Secondary Alkyllithiums Compounds and Trapping Reactions with Electrophiles », Angew. Chem. Int. Ed., 2014, 53, p. 1425-1429
  20. Bellan, A. B.; Knochel, P., « Highly Regioselective Remote Lithiation of Functionalized 1,3-bis-Silylated Arenes », Angew. Chem. Int. Ed., 2019, 58, p. 1838-1841
  21. Chen, Y.-H.; Ellwart, M.; Malakhov, V.; Knochel, P., « Solid organozinc pivalates: a new class of zinc organometallics with greatly enhanced air- and moisture-stability », Synthesis, 2017, 49, p. 3215-3223
  22. "Académie des sciences".
  23. "Leopoldina" (PDF).
  24. "Ordre du Mérite".
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