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.

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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

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

References

  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. 1 2 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. 1 2 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. 1 2 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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