Paul Knochel
Paul Knochel was born in 1955 in Strasbourg (France). He did his undergraduate studies at the University of
Strasbourg (France) and his Ph.D at the ETH-Zürich with Prof. D. Seebach. He spent 4 years at the CNRS at the
University Pierre and Marie Curie at Paris with Prof. J.-F.Normant and one year of post-doctoral studies at
Princeton University in the laboratory of Prof. M. F. Semmelhack. In 1987, he accepted a position as Assistant
Professor at the University of Michigan at Ann Arbor, Michigan. In 1991, he became Full Professor at this
University and in 1992, he moved to the Philipps-University at Marburg as C4-Professor in Organic Chemistry.
In 1999, he moved to the Chemistry Department of the Ludwig-Maximilians-University at Munich.
Our research interests are focussed on the development of new synthetic methods for organic and
heterocyclic chemistry using organometallic catalysts and reagents, the development of new reagents for
asymmetric catalysis. Especially, our research focussed on the preparation of polyfunctional zinc, magnesium
and copper reagents. Recently, new Mg- and Zn-bases have been prepared. They are powerful reagents for the
regioselective metalation of functionalized aromatics and heterocycles. Applications of these new methods to
natural product or biologically active compounds syntheses are performed.
Honors
Berthelot Medal of the Academie des 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 Académie des sciences (Paris) 2007
Member of the Bavarian Academy of Science 2008
Publications in recent three years.
388. Krasovskiy, A.; Straub, B.*; Knochel, P.* "Highly Efficient Reagents for the Br/Mg Exchange. Mechanisms, Preparation and Synthetic Applications" Angew. Chem. Int. Ed. 2006, 45, 159-162.
389. Stoll, A. H.; Krasovskiy, A.; Knochel, P.* "Preparation of Functionalized Benzylic Magnesium Reagents Using a New Sulfur-Magnesium Exchange Reaction" Angew. Chem. Int.Ed. 2006, 45, 606-609.
390. Krasovskiy, A.; Gavryushin, A.; Knochel, P.* "Higly stereoselective access to sulfur derivatives starting from zinc organometallics" Synlett, 2006, 792-794.
391. Krasovskiy, A.; Knochel, P.* "Convenient titration method of organometallic zinc, magnesium, and lanthanide reagents" Synthesis, 2006, 890-891.
392. Lin, W.; Ilgen, F.; Knochel, P.* "Preparation of highly functionalized arylmagnesium readents by the addition of magnesium phenyl selenide to arynes" Tetrahedron Lett., 2006, 47, 1941-1944.
393. Dunet, G.; Knochel, P.* "Iron- catalyzed cross-coupling between alkenyl and dienyl sulfonates and functionalized arylcooper reagents" Synlett, 2006, 407-410.
394. Kloetzing, R. J.; Thaler, T.; Knochel, P.* "Am improved Asymmetric Reformatsky Reaction Mediated by (-)-N,N-Dimethylaminoisoborneol" Org. Lett. 2006, 8, 1125-1128.
395. Ila, H.; Baron, O.; Wagner, A. J.; Knochel, P.* "Functionalized magnesium organometallics as versatile intermediates for the synthesis of polyfunctional heterocycles" Chem. Commun., 2006, 583-593.
396. Liu, C.-Y.; Ren; H.; Knochel, P.* "Magnesiated Unsaturated Silylated Cyanohygrins as Synthetic Equivalents of Aromatic and Heterocyclic Grignard Reagents Bearing a Ketone or a Aldehyde" Org. Lett. 2006,
8, 617-619.
397. Kloetzing, R.; Knochel, P.* "Ferrocenyl-QUINAP: a planar chiral P,N-ligand for palladium-catalized allylic substitution reactions" Tetrahedron: Asymmetry, 2006, 17, 116-123.
398. Ila, H.; Baron, O.; Wagner, A. J.; Knochel, P.* "Preparation and reactions of heteroaryl organomagnesium compounds" Chem. Lett., 2006, 35, 2-7.
399. Korn, T. J.; Schade, M. A.; Wirth, S.; Knochel, P.* "Cobalt (II)-Catalyzed Cross-Coupling between Polyfunctional Arylcopper Reagents and Aryl Fluorides or Tosylates" Org. Lett., 2006, 8, 725 -728.
400. Krasovskiy, A.; Kopp, F.; Knochel, P.* "New Soluble Lanthanide Salts (LnCl3.2LiCl; Ln = La, Ce, Nd) for the improved Addition of Magnesium Organometallics to Carbonyl Derivatives" Angew. Chem. Int. Ed.
Engl. 2006, 45, 497-500.
401. Ren, H.; Knochel, P.* “Regioselective Functionalization of Trisubstituted Pyridines Using a Bromine-Magnesium Exchange” Chem. Comm. 2006, 726-728.
402. Krasovskiy, A.; Krasovskaya, V.; Knochel, P.* „Mixed Mg/Li amides of the type R2NMgCl . LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds”
Angew. Chem. Int. Ed. Engl. 2006, 45, 2958-2961.
403. Yang, X.; Knochel, P.* „Selective functionalization of imidazoles via an iodine-copper exchange reaction” Chem. Comm. 2006, 2170-2172.
404. Boudet, N.; Knochel, P.* “Chemo- and Regioselective Functionalization of Uracil Derivatives. Applications to the Synthesis of Oxypurinol and Emivirine” Org. Lett. 2006, 8, 3737-3740.
405. Yang, X., Knochel, P.* “Stereoselective Preparation of Higly Functionalized (Z)-3-Copper Enoates by an Iodine-Copper Exchange Reaction” Synthesis 2006, 2167-2172.
406. Yang, X., Knochel, P.* “Direct Preparation of Copper organometallics Bearing an Aldehyde Function via an Iodine-Copper Exchange” Chem. Comm. 2006, 2486-2488.
407. Yang, X., Knochel, P.* “Preparation and Reactions of Functionalized Organocopper Reagents” Synthesis, 2006, 2618-2623.
408. Yang, X.; Knochel, P.* “Stereoselective Functionalization of β-iodo-ά,β-Unsaturated Ketones via an Iodine-Copper Exchange Reaction” Org. Lett. 2006, 8, 1941-1943.
409. Kofink, C. C.; Knochel, P.* “Synthesis of Functionalized Diarylmethanes via a Copper-Catalyzed Cross-Coupling of Arylmagnesium Reagents with Benzylic Phosphates” Org. Lett. 2006, 8, 4121-4124.
410. Sinha, P.; Kofink, C. C.; Knochel, P.* “Preparation of Aryl-Alkylamines via Electrophilic Amination of Functionalized Arylazo Tosylates with Alkylzinc Reagents” Org. Lett. 2006, 8, 3741-3744.
411. 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.
Engl. 2006, 45, 6040-6044.
412. Krasovskiy, A.; Tishkov, A.; del Amo, V.; Mayr, H.; Knochel, P.* “Transition-metal-free homocoupling of organomagnesium compounds” Angew. Chem. Int. Ed. Engl. 2006, 45, 5010-5014.
413. Gavryushin, A.; Kofink, C. C.; Manolikakes, G.; Knochel, P.* “An Efficient Negishi Cross-Coupling Reaction Catalyzed by Nickel(II) and Diethyl Phosphite” Tetrahedron 2006, 62, 7521-7533.
414. Soorukram, D.; Knochel, P.* “Copper-catalyzed Preparation of Ketones bearing a stereogenic center in α-position” Angew. Chem. Int. Ed. Engl. 2006, 45, 3686-3689.
415. Ren, H.; Knochel, P.* “Chemoselective Benzylic C-H Activations for the Preparation of Condenced N-heterocycles” Angew. Chem. Int. Ed. Engl. 2006, 45, 3462-3465.
416. Lin, W.; Baron, O.; Knochel, P.* “Highly Functionalized Benzene Syntheses by Directed Mono or Multiple Magnesiations with TMPMgCl.LiCl” Org. Lett. 2006, 8, 5673-5676.
417. Sinha, P., Knochel, P.* “Preparation of Polyfunctional Tertiary Amines via the Electrophilic Amination of Arylmagnesium Compounds Using N-Chloroamines” Synlett 2006, 3304-3308.
418. Del Amo, V.; Dubbaka, S. R.; Krasovskiy, A.; Knochel, P.* “General preparation of primary, secondary, and tertiary aryl amines by the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates”
Angew. Chem. Int. Ed. Engl. 2006, 45, 7838-7842.
419. 419. Korn, T. J.; Schade, M. A.; Cheemala, M. N.; Wirth, S.; Guevara, S. A.; Cahiez, G.; Knochel, Paul. “Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of
polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates.” Synthesis 2006, 3547-3574.
419-1. Knochel, P.*; Leuser, H.; Gong, L.-Z.; Perrone, S.; Kneisel, F. F. “Functionalized organozinc compounds” in Chemistry of Organozinc Compounds, Wiley Int. 2006, Pt. 1, 287-393, ISBN: 978-0-470-09337-5.
420. Krasnokutskaya, E. A.; Semenischeva, N. I.; Filimonov, V. D.; Knochel, P.* "A New, One-Step, Effective Protokol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines"
Synthesis, 2007, 81-84.
421. Soorukram, D.; Knochel, P.* “Formal Enantioselective Synthesis of (+)-Estrone” Org. Lett., 2007, 9, 1021-1023.
422. Soorukram, D.; Knochel, P.* “A Practical Synthesis of Optically Active α-Substituted Ketones in High Enantiomeric Excess” Synthesis 2007, 638-641.
423. Lin, W.; Chen, L.; Knochel, P.* “Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates” Tetrahedron 2007, 63, 2787-2797.
424. Ren, H.; Li, Z.; Knochel, P.* “Chemoselective C(sp3)-H Bond Activation for the Preparation of Condensed N-Heterocycles” Chem. Asian J. 2007, 2, 416-433.
425. Perrone, S.; Knochel, P.* “Highly Diastereoselective Preparation of (E)-Alkenylsilanes Bearing an α-Chiral Center.” Org. Lett. 2007, 9, 1041-1044.
426. Ren, H.; Dunet, G.; Mayer, P.; Knochel, P.* "Highly Diastereoselective Synthesis of Homoallylic Alcohols Bearing Adjacent Quaternary Centers Using Substituted Allylic Zinc Reagents" J. Am. Chem. Soc. 2007, 129,
5376-5377.
427. Kopp, F.; Knochel, P.* "Iodine-Magnesium Exchange on Unprotected Imidasoles in the Presence of LiCl" Synlett 2007, 0980-0982.
428. Kienle, M.; Dubbaka, S. R.; del Amo, V.; Knochel, P.* “Preparation of Tertiary Amines via the Oxidative Coupling Of Polyfunctional Aryl and Heteroaryl Amidocuprates" Synthesis 2007, 1272-1278.
429. Perrone, S.; Metzger, A.; Knochel, P.* "Chiral Allylic Cyanohydrins as Versatile Substrates for Diastereoselective Copper(I)-mediated SN2' Allylic Substitutions" Synlett 2007, 1047-1050.
430. Kopp, F.; Knochel, P.* "Functionalisation of Unprotected Uracil Derivatives Using the Halogen-Magnesium Exchange" Org. Lett. 2007, 9, 1639-1641.
431. Kopp, F.; Wunderlich, S.; Knochel, P.* "Halogen-magnesium exchange on unprotected aromatic and heteroaromatic carboxylic acids" Chem. Comm. 2007, 2075-2077.
432. Dunet, G.; Knochel, P.* "Highly Stereoselective Cobalt-Catalyzed Allylation of Functionalized Diarylzinc Reagents” Synlett 2007, 1383-1386.
433. Liron, F.; Knochel, P.* "Reactivity of stable neopentyl-Pd intermediates in the absence of nucleophile" Tetrahedron Lett. 2007, 48, 4943-4946.
434. Cheemala, M. N.; Knochel, P.* "New P,N-Ferrocenyl Ligands for the Asymmetric Ir-Catalyzed Hydrogenation of Imines" Org. Lett. 2007, 9, 3089-3092.
435. Kofink, C. C.; Blank, B.; Pagano, S.; Goetz, N.; Knochel, P.* "Iron-catalyzed aryl-aryl cross-coupling reaction tolerating amides and unprotected quinolinones" Chem. Comm. 2007, 1954-1956.
436. Liu, C.-Y.; Knochel, P.* „Preparation of Polyfunctional Aryl Triazenes via a Direct Insertion Reaction of Zn in the Presence of LiCl” Synlett 2007, 2081-2085.
437. Manolikakes, G.; Dastbaravardeh, N.; Knochel, P.* „Nickel-Catalyzed Cross-Coupling Reactions of Aryltitanium(IV) Alkoxides with Aryl Halides” Synlett 2007, 2077-2080.
438. Liu, C.-Y.; Gavryushin, A.; Knochel, P.* „Synthesis of functionalized o-, m-, and p-terphenyl derivatives by consecutive cross-coupling reactions of triazene-substituted arylboronic esters.” Chem. Asian J. 2007, 2,
1020-1030.
439. Liu, C.-Y.; Knochel, P.* „Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9-Methoxyellipticine, Isoellipticine, and 7-Carbethoxyisoellipticine” J. Org. Chem. 2007, 72,
7106-7115.
440. Wunderlich, S. H.; Knochel, P.* “(tmp)2Zn•2MgCl2•2LiCl: a chemoselective base for the directed zincation of sensitive arenes and heteroarenes” Angew. Chem. Int. Ed. 2007, 46, 7685-7688.
441. Clososki, G. C.; Rohbogner, C. J.; Knochel, P.* “Direct magnesiation of polyfunctionalized arenes and heteroarenes using (tmp)2Mg•2LiCl” Angew. Chem. Int. Ed. 2007, 46, 7681-7684.
442. Gommermann, N.; Knochel, P.* “N,N-Dibenzyl-N-[1-cyclohexyl-3-(trimethylsilyl)-2-propynyl]-amine from cyclohexanecarbaldehyde, trimethylsilylacetylene and dibenzylamine” Org. Synth. 2007, 84, 1-10.
443. Fleming, F. F.; Gudipati, S.; Vu, V. A.; Mycka, R. J.; Knochel, P.* “Grignard Reagents: Alkoxide-Directed Iodine-Magnesium Exchange at sp3 Centers” Org. Lett. 2007, 9, 4507-4509.
444. Boudet, N.; Sase, S.; Sinha, P.; Liu, C.-Y.; Krasovskiy, A.; Knochel, P.* “Directed Ortho Insertion (DoI): A New Approach to Functionalized Aryl and Heteroaryl Zinc Reagents” J. Am. Chem. Soc. 2007, 129, 1235812359.
445. Kienle, M.; Dubbaka, S. R.; Brade, K.; Knochel, P.* “Modern amination reactions” Eur. J. Org. Chem. 2007, 25, 4166-4176.
446. Thaler, T.; Geittner, F.; Knochel, P.* „A Novel Synthetic Approach towards Chiral QUINAP via Diastereometric Sulfoxide Intermediates” Synlett 2007, 2655-2658.
447. Melzig, L.; Gavryushin, A.; Knochel, P.* „Direct Aminoalkylation of Arenes and Hetarenes via Ni-Catalyzed Negishi Cross-Coupling Reactions” Org. Lett. 2007, 9, 5529-5532.
448. Soorukram, D.; Boudet, N.; Malakhov, V.; Knochel, P.* “Preparation of polyfunctionalized 2,6-dimethoxypyrimidine derivatives via chemo- and regioselective direct zinc insertion” Synthesis 2007, 3915-3922.
449. Cheemala, M. N.; Gayral, M.; Brown, J. M.; Rossen, K.; Knochel, P.* “New paracyclophane phosphine for highly enantioselective ruthenium-catalyzed hydrogenation of prochiral ketones” Synthesis 2007, 38773885.
450. Kolodney, G.; Sklute, G.; Perrone, S.; Knochel, P.*; Marek, I. “Diastereodivergent synthesis of enantiomerically pure homoallylic amine derivatives containing quaternary carbon stereocenters” Angew. Chem. Int.
Ed. 2007, 46, 9291-9294.
451. Dubbaka, S. R.; Kienle, M.; Mayr, H.; Knochel, P.* “Copper (I)-mediated oxidative cross-coupling between functionalized alkynyl lithium and Aryl magnesium reagents” Angew. Chem. Int. Ed. 2007, 46, 9093-9096.
452. Boudet, N.; Lachs, J. R.; Knochel, P.* “Multiple Regioselective Functionalizations of Quinolines via Magnesiations” Org. Lett. 2007, 9, 5525-5528.
453. Stoll, A. H.; Mayer, P.; Knochel, P.* “Preparation of Di-, Tri-, and Tetra-Substituted Functionalized Ferrocenes via Magnesium Organometallics” Organometallics 2007, 26, 6694-6697.
454. Shi, L.; Chu, Y.; Knochel, P.*; Mayr, H. “Relative rates of bromine-magnesium exchange reactions in substituted bromobenzene derivatives” Angew. Chem. Int. Ed. 2008, 47, 202-204.
455. Stoll, A. H.; Knochel, P.* “Preparation of Fully Substituted Anilines for the Synthesis of Functionalized Indoles” Org. Lett. 2008, 10, 113-116.
456. Manolikakes, G.; Gavryushin, A.; Knochel, P.* “An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides” J. of Org. Chem. 2008, 73, 1429-1434.
457. Dunet, G.; Mayer, P.; Knochel, P.* “Highly Diastereoselective Addition of Cinnamylzinc Derivatives to α-Chiral Carbonyl Compounds” Org. Lett. 2008, 10, 117-120.
458. Abu Thaher, B.; Koch, P.; del Amo, V.; Knochel, P.; Laufer, S.* „A Convenient Synthesis of 1-(4-Fluorophenyl)-2-(4-pyridyl)cyclopentene from Cyclopentanone” Synthesis 2008, 225-228.
459. Druzhinin, S. I.; Dubbaka, S. R.; Knochel, P.*; Kovalenko, S. A.; Mayer, P.; Senyushkina, T.; Zachariasse, K. A. “Ultrafast Intramolecular Charge Transfer with Strongly Twisted Aminobenzonitriles: 4-(Di-tertbutylamino) benzonitrile and 3-(Di-tert-butylamino) benzonitrile” J. of Phys. Chem. A 2008, 112, 2749-2761.
460. Rohbogner, C. J.; Clososki, G.; Knochel, P.* “A general method for meta- and para- functionalization of arenes using TMP2Mg • 2 LiCl” Angew. Chem. Int. Ed. 2008, 47, 1503-1507.
461. Metzger, A.; Schade, M. A.; Knochel, P.* “LiCl-Mediated Preparation of Highly Functionalized Benzylic Zinc Chlorides” Org. Lett. 2008, 10, 1107-1110.
462. Rauhut, C. B.; Vu, V. A.; Fleming, F. F.; Knochel, P.* “Preparation of Functionalized Alkylmagnesium Derivatives Using an I/Mg-Exchange” Org. Lett. 2008, 10, 1187-1189.
463. Ireland, T.; Tappe, K.; Grossheimann, G.; Knochel, P.* “Synthesis of a new class of chiral 1,5-diphosphanylferrocenyl ligands and their use in enantioselective hydrogenation” Chem. Eur. J. 2008, 14(12), 3509.
464. Tappe, K.; Knochel P.* “New Efficient Synthesis of Taniaphos-Ligands. Application in Ruthenium- and Rhodium-Catalyzed Enantioselective Hydrogenations” [Tetrahedron: Asymmetry 2004, 15, 91-102]
Tetrahedron: Asymmetry 2008, 19, 891.
465. Despotopoulou, C.; Bauer, R. C.; Krasovskiy, A.; Mayer, P.; Stryker, J. M.; Knochel, P.* “Selective mono- and 1,2-difunctionalisation of cyclopentene derivatives via Mg and Cu intermediates” Chem. Eur. J. 2008,
14(8), 2499-2506.
466. Helm, M. D.; Mayer, P.; Knochel, P.* “Preparation of silyl substituted crotylzinc reagents and their highly diastereoselective addition to carbonyl compounds” Chem. Comm. 2008, 16, 1916-1917.
467. Boudet, N.; Dubbaka, S. R.; Knochel, P.* “Oxidative Amination of Cuprated Pyrimidine and Purine Derivatives” Org. Lett. 2008, 10, 1715-1718.
468. Schade, M. A.; Metzger, A.; Hug, S.; Knochel, P.* “Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates” Chem. Comm. 2008, 26, 3046-3048.
469. Manolikakes, G.; Schade, M. A.; Munoz Hernandez, C.; Mayr, H.; Knochel, P.* “Negishi Cross-Couplings of Unsaturated Halides Bearing Relatively Acidic Hydrogen Atoms with Organozinc Reagents” Org. Lett. 2008,
10, 2765-2768.
470. Ireland, T; Grossheimann, G; Wieser-Jeunesse, C; Knochel, P.* positions for ,“Ferrocenyl ligands with two phosphanyl substituents in the the transition metal catalyzed asymmetric hydrogenation of
functionalized double bonds” [Erratum to document cited in CA132:122132]. Angew. Chem. Int. Ed. 2008, 47, 3666.
471. Mosrin, M.; Knochel, P.* „Regio- and Chemoselective Multiple Functionalization of Pyrimidine Derivatives by Selective Magnesiations using LiCl” Org. Lett. 2008, 10, 2497-2500.TMPMgCl