Herbert Mayr

Summary

Affiliation: University of Munich
Country: Germany

Publications

  1. ncbi request reprint Reference scales for the characterization of cationic electrophiles and neutral nucleophiles
    H Mayr
    Department Chemie der Ludwig Maximilians Universität München, Butenandtstrasse 5 13 Haus F, D 81377 Munchen, Germany
    J Am Chem Soc 123:9500-12. 2001
  2. ncbi request reprint The reactivity-selectivity principle: an imperishable myth in organic chemistry
    Herbert Mayr
    Department Chemie und Biochemie, Ludwig Maximilians Universitat Munchen, Germany
    Angew Chem Int Ed Engl 45:1844-54. 2006
  3. ncbi request reprint Pi-nucleophilicity in carbon-carbon bond-forming reactions
    Herbert Mayr
    Department Chemie der Ludwig Maximilians Universität, Butenandtstrasse 5 13 Haus F, D 81377 Munchen, Germany
    Acc Chem Res 36:66-77. 2003
  4. ncbi request reprint Counterion effects in iminium-activated electrophilic aromatic substitutions of pyrroles
    Sami Lakhdar
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13 Haus F, 81377 Munchen, Germany
    Chem Commun (Camb) 47:1866-8. 2011
  5. doi request reprint Farewell to the HSAB treatment of ambident reactivity
    Herbert Mayr
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 Munchen, Germany
    Angew Chem Int Ed Engl 50:6470-505. 2011
  6. ncbi request reprint Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates
    Sami Lakhdar
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13 Haus F, 81377 Munchen, Germany
    Chem Commun (Camb) 48:4504-6. 2012
  7. pmc Crystal structure of (1S,2R)-6,6-dimethyl-4,8-dioxo-2-phenyl-spiro-[2.5]octane-1-carbaldehyde
    Saloua Chelli
    Ludwig Maximilians Universitat, Department, Butenandtstrasse 5 13, 81377 Munchen, Germany
    Acta Crystallogr E Crystallogr Commun 72:266-8. 2016
  8. doi request reprint Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential
    Saloua Chelli
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 Munchen, Germany
    J Am Chem Soc 138:10304-13. 2016
  9. pmc Crystal structure of 2-[chloro-(4-meth-oxy-phen-yl)meth-yl]-2-(4-meth-oxy-phen-yl)-5,5-di-methyl-cyclo-hexane-1,3-dione
    Saloua Chelli
    Department Chemie und Biochemie, Ludwig Maximilians Universitat, Butenandtstrasse 513, D 81377 Munchen, Germany
    Acta Crystallogr E Crystallogr Commun 72:300-3. 2016
  10. doi request reprint Stereoselective synthesis and reactions of secondary alkyllithium reagents functionalized at the 3-position
    Kohei Moriya
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13, 81377 München Germany
    Angew Chem Int Ed Engl 54:2754-7. 2015

Collaborators

  • Sami Lakhdar
  • Lei Shi
  • Guillaume Berionni
  • Peter Mayer
  • Biplab Maji
  • Saloua Chelli
  • Armin R Ofial
  • Peter A Byrne
  • Konstantin Troshin
  • Paul Knochel
  • Konstantin Karaghiosoff
  • Hendrik Zipse
  • Quan Chen
  • Kohei Moriya
  • Francisco Corral-Bautista
  • Johannes Ammer
  • Hannes Erdmann
  • Xingwei Guo
  • Annette Frischmuth
  • Xi Chen
  • Christian F Sailer
  • Dominik S Allgäuer
  • Markus Horn
  • Ernst Ulrich Würthwein
  • Shinjiro Kobayashi
  • Lucien Eisenburger
  • Hiroaki Kurouchi
  • Jeffrey M Hammann
  • Meike Simon
  • Dorian Didier
  • Artem I Leonov
  • Lydia Klier
  • Nadja M Barl
  • Feng An
  • Yue Tan
  • Florian Achrainer
  • Maitane Fernández
  • Benjamin P Fingerhut
  • Gabriele Lang-Wittkowski
  • Varvara Morozova
  • Sebastian Thallmair
  • Ludwig H Schappele
  • Maximilian Heininger
  • Christoph Nolte
  • Eberhard Riedle
  • Regina de Vivie-Riedle
  • Igor Pugliesi

Detail Information

Publications34

  1. ncbi request reprint Reference scales for the characterization of cationic electrophiles and neutral nucleophiles
    H Mayr
    Department Chemie der Ludwig Maximilians Universität München, Butenandtstrasse 5 13 Haus F, D 81377 Munchen, Germany
    J Am Chem Soc 123:9500-12. 2001
    ..19 to -2.11, i.e., in a range with only very few previous entries...
  2. ncbi request reprint The reactivity-selectivity principle: an imperishable myth in organic chemistry
    Herbert Mayr
    Department Chemie und Biochemie, Ludwig Maximilians Universitat Munchen, Germany
    Angew Chem Int Ed Engl 45:1844-54. 2006
    ..This Minireview shows why selectivity cannot generally decrease with increasing reactivity and highlights the weaknesses of the theoretical foundations of the RSP...
  3. ncbi request reprint Pi-nucleophilicity in carbon-carbon bond-forming reactions
    Herbert Mayr
    Department Chemie der Ludwig Maximilians Universität, Butenandtstrasse 5 13 Haus F, D 81377 Munchen, Germany
    Acc Chem Res 36:66-77. 2003
    ..We outline how new compounds can be added to the scales and present our view on the scope and limitations of this approach to polar organic reactivity...
  4. ncbi request reprint Counterion effects in iminium-activated electrophilic aromatic substitutions of pyrroles
    Sami Lakhdar
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13 Haus F, 81377 Munchen, Germany
    Chem Commun (Camb) 47:1866-8. 2011
    ....
  5. doi request reprint Farewell to the HSAB treatment of ambident reactivity
    Herbert Mayr
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 Munchen, Germany
    Angew Chem Int Ed Engl 50:6470-505. 2011
    ..An alternative treatment of ambident reactivity based on Marcus theory will be presented...
  6. ncbi request reprint Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates
    Sami Lakhdar
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13 Haus F, 81377 Munchen, Germany
    Chem Commun (Camb) 48:4504-6. 2012
    ..Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals...
  7. pmc Crystal structure of (1S,2R)-6,6-dimethyl-4,8-dioxo-2-phenyl-spiro-[2.5]octane-1-carbaldehyde
    Saloua Chelli
    Ludwig Maximilians Universitat, Department, Butenandtstrasse 5 13, 81377 Munchen, Germany
    Acta Crystallogr E Crystallogr Commun 72:266-8. 2016
    ..In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π contacts resulting in a three-dimensional supra-molecular structure. ..
  8. doi request reprint Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential
    Saloua Chelli
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 Munchen, Germany
    J Am Chem Soc 138:10304-13. 2016
    ....
  9. pmc Crystal structure of 2-[chloro-(4-meth-oxy-phen-yl)meth-yl]-2-(4-meth-oxy-phen-yl)-5,5-di-methyl-cyclo-hexane-1,3-dione
    Saloua Chelli
    Department Chemie und Biochemie, Ludwig Maximilians Universitat, Butenandtstrasse 513, D 81377 Munchen, Germany
    Acta Crystallogr E Crystallogr Commun 72:300-3. 2016
    ..The packing features inversion dimers formed by pairs of C-H⋯O contacts and strands along [100] and [010] established by further C-H⋯O and C-H⋯Cl contacts, respectively. ..
  10. doi request reprint Stereoselective synthesis and reactions of secondary alkyllithium reagents functionalized at the 3-position
    Kohei Moriya
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13, 81377 München Germany
    Angew Chem Int Ed Engl 54:2754-7. 2015
    ..Kinetic studies show that the 3-siloxy group strongly accelerates the epimerization at the lithium-substituted carbon atom. This method offers a new way to construct chiral open-chain molecules with excellent stereoselectivity. ..
  11. doi request reprint Scales of Lewis basicities toward C-centered Lewis acids (carbocations)
    Herbert Mayr
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstraße 5 13, Haus F, 81377 Munchen, Germany
    J Am Chem Soc 137:2580-99. 2015
    ..The boundaries of linear rate-equilibrium relationships were thus defined. ..
  12. doi request reprint Fine-tuning the nucleophilic reactivities of boron ate complexes derived from aryl and heteroaryl boronic esters
    Guillaume Berionni
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 München Germany http www cup uni muenchen de oc mayr
    Angew Chem Int Ed Engl 54:2780-3. 2015
    ..The neopentyl and ethylene glycol derivatives were found to be 10(4) times more reactive than the pinacol and catechol derivatives. ..
  13. doi request reprint Structures and reactivities of 2-Trityl- and 2-(Triphenylsilyl)pyrrolidine-derived enamines: evidence for negative hyperconjugation with the trityl group
    Hannes Erdmann
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 Munchen, Germany
    J Am Chem Soc 136:14263-9. 2014
    ..The consequences of these observations for the rationalization of the reactivity of the Jørgensen-Hayashi catalyst (diphenylprolinol trimethylsilyl ether) are discussed. ..
  14. doi request reprint Ambident Reactivity of Acetyl- and Formyl-Stabilized Phosphonium Ylides
    Peter A Byrne
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstraße 5 13, 81377 Munchen, Germany
    J Am Chem Soc 138:11272-81. 2016
    ....
  15. doi request reprint New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts
    Annette Frischmuth
    Ludwig Maximilians Universitat Munchen, Department Chemie, Butenandtstrasse 5 13, Haus F, 81377 München Germany
    Angew Chem Int Ed Engl 53:7928-32. 2014
    ....
  16. doi request reprint Di- and triarylmethylium ions as probes for the ambident reactivities of carbanions derived from 5-benzylated Meldrum's acid
    Xi Chen
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13, 81377 München Germany
    Chemistry 20:11069-77. 2014
    ....
  17. doi request reprint A comprehensive microscopic picture of the benzhydryl radical and cation photogeneration and interconversion through electron transfer
    Christian F Sailer
    Lehrstuhl fur BioMolekulare Optik, Ludwig Maximilians Universitat Munchen, Oettingenstr 67, 80538 Munchen, Germany
    Chemphyschem 14:1423-37. 2013
    ..The results demonstrate that, at least for aprotic solvents, traditional descriptions of reaction mechanisms based on the concept of contact and solvent-separated pairs have to be reassessed...
  18. doi request reprint Electrophilic aromatic substitutions of aryltrifluoroborates with retention of the BF3- group: quantification of the activating and directing effects of the trifluoroborate group
    Guillaume Berionni
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13 Haus F, 81377 Munchen, Germany
    J Am Chem Soc 135:6317-24. 2013
    ..Remote reactions of heteroaryl trifluoroborates with iminium ions provide straightforward access to novel zwitterionic ammonium or iminium trifluoroborates, which have been characterized by single-crystal X-ray analyses...
  19. doi request reprint Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?
    Quan Chen
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, Haus F, 81377, Munchen, Germany
    Angew Chem Int Ed Engl 55:12664-7. 2016
    ..Its predicted usability as a reagent in electrophilic aromatic substitutions with electron-rich arenes was confirmed by uncatalyzed reactions with alkyl-substituted pyrroles. ..
  20. doi request reprint Nucleophilicity of Alkyl Zirconocene and Titanocene Precatalysts, and Kinetics of Activation by Carbenium Ions and by B(C6 F5 )3
    Guillaume Berionni
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstr 5 13, 81377, Munchen, Germany
    Chemistry 22:11196-200. 2016
    ....
  21. ncbi request reprint Reactions of carbocations with unsaturated hydrocarbons: electrophilic alkylation or hydride abstraction?
    Herbert Mayr
    Department Chemie der Ludwig Maximilians Universität München, Butenandtstrasse 5 13 Haus F, D 81377 Munchen, Germany
    J Am Chem Soc 124:4076-83. 2002
    ....
  22. doi request reprint Philicities, Fugalities, and Equilibrium Constants
    Herbert Mayr
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 Munchen, Germany
    Acc Chem Res 49:952-65. 2016
    ..The need to systematically analyze the role of intrinsic barriers is emphasized. ..
  23. doi request reprint Why Are Vinyl Cations Sluggish Electrophiles?
    Peter A Byrne
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 Munchen, Germany
    J Am Chem Soc . 2017
    ....
  24. doi request reprint Mechanisms of hydride abstractions by quinones
    Xingwei Guo
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstraße 5 13 Haus F, 81377 Munchen, Germany
    J Am Chem Soc 136:13863-73. 2014
    ....
  25. doi request reprint From Carbanions to Organometallic Compounds: Quantification of Metal Ion Effects on Nucleophilic Reactivities
    Francisco Corral-Bautista
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 München Germany
    Angew Chem Int Ed Engl 54:12497-500. 2015
    ....
  26. doi request reprint Ambident reactivities of formaldehyde n,n-dialkylhydrazones
    Biplab Maji
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 München Germany
    Angew Chem Int Ed Engl 52:11900-4. 2013
    ....
  27. doi request reprint Leaving group dependence of the rates of halogen-magnesium exchange reactions
    Lei Shi
    the Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, China, and Department Chemie der Ludwig Maximilians Universität München, Butenandtstrasse 5 13 Haus F, München 81377, Germany
    Org Lett 14:2602-5. 2012
    ..Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10(4) times more slowly than a bromide. ..
  28. doi request reprint Structures and ambident reactivities of azolium enolates
    Biplab Maji
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 München Germany http www cup uni muenchen de oc mayr
    Angew Chem Int Ed Engl 52:11163-7. 2013
    ..Kinetic studies show that the enolate oxygen is 20 times more nucleophilic than the carbon atom, but under thermodynamic control exclusive C-addition products were formed. ..
  29. doi request reprint Nucleophilicity parameters of pyridinium ylides and their use in mechanistic analyses
    Dominik S Allgäuer
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13, 81377 Munchen, Germany
    J Am Chem Soc 135:15216-24. 2013
    ..Deviations between calculated and experimental rate constants by a factor of 10(6) were demonstrated to indicate a change of reaction mechanism...
  30. pmc 5-[(E)-Meth-oxy(phen-yl)methyl-idene]-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole
    Biplab Maji
    Ludwig Maximilians Universitat, Department Chemie und Biochemie, Butenandtstrasse 5 13, 81377 Munchen, Germany
    Acta Crystallogr Sect E Struct Rep Online 68:o3307. 2012
    ..The dihedral angles between the four phenyl rings and the 1,2,4-triazole ring are 31.01 (10), 49.01 (8), 78.55 (6) and 41.51 (9)°. In the crystal, mol-ecules are linked along [100] by weak C-H⋯O hydrogen bonds...
  31. doi request reprint Towards a comprehensive hydride donor ability scale
    Markus Horn
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 Munchen, Germany
    Chemistry 19:249-63. 2013
    ....
  32. pmc A quantitative approach to nucleophilic organocatalysis
    Herbert Mayr
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandstr 5 13 Haus F, 81377 Munchen, Germany
    Beilstein J Org Chem 8:1458-78. 2012
    ..O-Methylated Breslow intermediates are a hundred-fold less nucleophilic than deoxy Breslow intermediates...
  33. ncbi request reprint Structures and reactivities of o-methylated breslow intermediates
    Biplab Maji
    Department Chemie, Ludwig Maximilians Universitat Munchen, Butenandtstrasse 5 13 Haus F, 81377 München Germany http www cup lmu de oc mayr
    Angew Chem Int Ed Engl 51:10408-12. 2012
    ..A series of these compounds have been synthesized, their structures determined, and the kinetics of their reactions with electrophiles investigated...
  34. doi request reprint Generation of α,β-unsaturated iminium ions by laser flash photolysis
    Sami Lakhdar
    Department Chemie, Ludwig Maximilians Universitat Munchen, Germany
    Angew Chem Int Ed Engl 50:9953-6. 2011
    ..The rate constants of their reactions with nucleophiles provide the first direct comparison of the electrophilicities of iminium ions derived from MacMillan's first- and second-generation catalysts...