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Paul Knochel

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

Biography

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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

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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] 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

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  • 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

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  1. ^ "LMU München – Curriculum Vitae". Group of Prof. Paul Knochel. 16 December 2021. Retrieved 16 December 2021.
  2. ^ "Prof. Dr. Paul Knochel". Faculty for Chemistry and Pharmacy LMU Munich. Retrieved 16 December 2021.
  3. ^ Ellwart, Mario; Knochel, Paul (17 July 2015). "Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles". Angewandte Chemie International Edition. 54 (36). Wiley: 10662–10665. doi:10.1002/anie.201504354. ISSN 1433-7851. PMID 26189654.
  4. ^ Blümke, Tobias; Chen, Yi-Hung; Peng, Zhihua; Knochel, Paul (24 March 2010). "Preparation of functionalized organoaluminiums by direct insertion of aluminium to unsaturated halides". Nature Chemistry. 2 (4). Springer Science and Business Media LLC: 313–318. Bibcode:2010NatCh...2..313B. doi:10.1038/nchem.590. ISSN 1755-4330. PMID 21124514. S2CID 5280421.
  5. ^ Krasovskiy, Arkady; Knochel, Paul (21 June 2004). "A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides". Angewandte Chemie International Edition. 43 (25). Wiley: 3333–3336. doi:10.1002/anie.200454084. ISSN 1433-7851. PMID 15213967.
  6. ^ Krasovskiy, Arkady; Malakhov, Vladimir; Gavryushin, Andrei; Knochel, Paul (11 September 2006). "Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides". Angewandte Chemie International Edition. 45 (36). Wiley: 6040–6044. doi:10.1002/anie.200601450. ISSN 1433-7851. PMID 16900548.
  7. ^ Kneisel, Florian F.; Dochnahl, Maximilian; Knochel, Paul (13 February 2004). "Nucleophilic Catalysis of the Iodine–Zinc Exchange Reaction: Preparation of Highly Functionalized Diaryl Zinc Compounds". Angewandte Chemie International Edition. 43 (8). Wiley: 1017–1021. doi:10.1002/anie.200353316. ISSN 1433-7851. PMID 14966896.
  8. ^ a b Ziegler, Dorothée S.; Karaghiosoff, Konstantin; Knochel, Paul (28 May 2018). "Generation of Aryl and Heteroaryl Magnesium Reagents in Toluene by Br/Mg or Cl/Mg Exchange". Angewandte Chemie International Edition. 57 (22). Wiley: 6701–6704. doi:10.1002/anie.201802123. ISSN 1433-7851. PMID 29656503.
  9. ^ Makarov, Ilya S.; Brocklehurst, Cara E.; Karaghiosoff, Konstantin; Koch, Guido; Knochel, Paul (30 August 2017). "Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para ‐Disubstituted Benzenes from [1.1.1]Propellane". Angewandte Chemie International Edition. 56 (41). Wiley: 12774–12777. doi:10.1002/anie.201706799. ISSN 1433-7851. PMID 28786520.
  10. ^ Haag, Benjamin; Mosrin, Marc; Ila, Hiriyakkanavar; Malakhov, Vladimir; Knochel, Paul (27 September 2011). "Regio- and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases". Angewandte Chemie International Edition. 50 (42). Wiley: 9794–9824. doi:10.1002/anie.201101960. ISSN 1433-7851. PMID 21953742.
  11. ^ Chen, Yi-Hung; Graßl, Simon; Knochel, Paul (28 December 2017). "Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N -Hydroxylamine Benzoates". Angewandte Chemie International Edition. 57 (4). Wiley: 1108–1111. doi:10.1002/anie.201710931. ISSN 1433-7851. PMID 29160920.
  12. ^ Weidmann, Niels; Ketels, Marthe; Knochel, Paul (13 August 2018). "Sodiation of Arenes and Heteroarenes in Continuous Flow". Angewandte Chemie International Edition. 57 (33). Wiley: 10748–10751. doi:10.1002/anie.201803961. ISSN 1433-7851. PMID 29873427.
  13. ^ Ganiek, Maximilian A.; Becker, Matthias R.; Berionni, Guillaume; Zipse, Hendrik; Knochel, Paul (17 July 2017). "Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation". Chemistry – A European Journal. 23 (43). Wiley: 10280–10284. doi:10.1002/chem.201702593. ISSN 0947-6539. PMID 28590518.
  14. ^ Becker, Matthias R.; Ganiek, Maximilian A.; Knochel, Paul (2015). "Practical and economic lithiations of functionalized arenes and heteroarenes using Cy2NLi in the presence of Mg, Zn or La halides in a continuous flow". Chemical Science. 6 (11). Royal Society of Chemistry (RSC): 6649–6653. doi:10.1039/c5sc02558c. ISSN 2041-6520. PMC 5802273. PMID 29435214.
  15. ^ a b Chen, Yi-Hung; Ellwart, Mario; Toupalas, Georgios; Ebe, Yusuke; Knochel, Paul (22 March 2017). "Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability". Angewandte Chemie International Edition. 56 (16). Wiley: 4612–4616. doi:10.1002/anie.201700216. ISSN 1433-7851. PMID 28326665.
  16. ^ Becker, Matthias R.; Knochel, Paul (14 May 2015). "Practical Continuous-Flow Trapping Metalations of Functionalized Arenes and Heteroarenes Using TMPLi in the Presence of Mg, Zn, Cu, or La Halides". Angewandte Chemie International Edition. 54 (42). Wiley: 12501–12505. doi:10.1002/anie.201502393. ISSN 1433-7851. PMID 25973885.
  17. ^ Stathakis, Christos I.; Bernhardt, Sebastian; Quint, Valentin; Knochel, Paul (21 August 2012). "Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings". Angewandte Chemie International Edition. 51 (37). Wiley: 9428–9432. doi:10.1002/anie.201204526. ISSN 1433-7851. PMID 22907878.
  18. ^ a b Morozova, Varvara; Skotnitzki, Juri; Moriya, Kohei; Karaghiosoff, Konstantin; Knochel, Paul (30 March 2018). "Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper Reagents-Synthesis of (−)-Lardolure and Siphonarienal". Angewandte Chemie International Edition. 57 (19). Wiley: 5516–5519. doi:10.1002/anie.201800792. ISSN 1433-7851. PMID 29512307.
  19. ^ Dagousset, Guillaume; Moriya, Kohei; Mose, Rasmus; Berionni, Guillaume; Karaghiosoff, Konstantin; Knochel, Paul (20 December 2013). "Diastereoselective Synthesis of Open-Chain Secondary Alkyllithium Compounds and Trapping Reactions with Electrophiles". Angewandte Chemie International Edition. 53 (5). Wiley: 1425–1429. doi:10.1002/anie.201308679. ISSN 1433-7851. PMID 24459059.
  20. ^ Bellan, Andreas B.; Knochel, Paul (11 January 2019). "Highly Regioselective Remote Lithiation of Functionalized 1,3‐bis‐Silylated Arenes". Angewandte Chemie International Edition. 58 (6). Wiley: 1838–1841. doi:10.1002/anie.201812742. ISSN 1433-7851. PMID 30548961. S2CID 56485145.
  21. ^ Chen, Yi-Hung; Ellwart, Mario; Malakhov, Vladimir; Knochel, Paul (29 May 2017). "Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability". Synthesis. 49 (15). Georg Thieme Verlag KG: 3215–3223. doi:10.1055/s-0036-1588843. ISSN 0039-7881. S2CID 98932526.
  22. ^ "Paul Knochel – Listes par ordre alphabétique – Listes des membres – Membres – Nous connaître". Liste des membres de l'Académie des sciences / K (in French). Retrieved 16 December 2021.
  23. ^ "Leopoldina" (PDF).
  24. ^ "Ordre du Mérite".
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