Publications

70. Pertechnetates – a structural study across the periodic table
E. Strub,* D. Grödler,* D. Zaratti, C. Yong, L. Dünnebier, S. Bazhenova, M. Roca Jungfer, M. Breugst,* M. Zegke* Chem. Eur. J., 2024, 30, accepted.
DOI: 10.1002/chem.202400131

69. Two distinct protocols for the synthesis of unsymmetrical 3,4-disubstituted maleimides based on transition-metal catalysts
F. Bandehali-Naeini, Z. Tanbakouchian, N. Farajinia-Lehi, N. Mayer, M. Shiri,* M. Breugst,* Org. Biomol. Chem., 2024, 22, 380–387.
DOI: 10.1039/D3OB01620J

68. Concepts and Practical Aspects of Computational Chemistry (Book Chapter)
M. Breugst, in Enabling Tools and Techniques for Organic Synthesis (Ed. S. G. Newman), 2023, 259–311.
DOI: 10.1002/9781119855668.ch7
ISBN (print): 978-1-119-85563-7

67. Divergent synthesis of pyrrole carboxamides from pyrrole carboxaldehyde and formamides /amines via oxidative amidation involving pyrrole acyl radicals
J. K. Laha,* S. Panday, J. P. Weber, M. Breugst,* Chem. Commun., 2023, 60, 10259–10262.
DOI: 10.1039/D3CC02766J

66. Transition Metal-Free Regioselective Phosphonation of Pyridines: Scope and Mechanism
V. Quint, T. H. V. Nguyen, G. Mathieu, S. Chelli, M. Breugst,* J.-F. Lohier, A.-C. Gaumont,S. Lakhdar,* ACS Org. Inorg. Au, 2023, 3, 151–157.
DOI: 10.1021/acsorginorgau.2c00055

65. Iodine-Catalyzed Claisen-Rearrangements of Allyl Aryl Ethers and Subsequent Iodocyclizations
T. Arndt, A. Raina, M. Breugst,* Chem. Asian J., 2023, 18, e202201279.
DOI: 10.1002/asia.202201279

64. TBHP-Mediated Denitrogenative Synthesis of Pyridine Carboxamides from Pyridine Carbohydrazides and Amines in Water
J. K. Laha,* A. Gupta, U. Gulati, M. K. Hunjan, J. P. Weber, M. Breugst,* Org. Chem. Front., 2022, 9, 6902–5908.
DOI: 10.1039/D2QO01465C

63. Stereoselective Synthesis of 2-Oxyenamides
S.-C. Krieg, J. Grimmer, A. M. Pick, H. Kelm, M. Breugst, G. Manolikakes, Eur. J. Org. Chem., 2022, e202200772.
DOI: 10.1002/ejoc.202200772

62. pH-Controlled Intramolecular Decarboxylative Cyclization of Biarylacetic Acids: Implication on Umpolung Reactivity of Aroyl Radicals
J. K. Laha,* U. Gulati, Saima, T. Schulte, M. Breugst,* J. Org. Chem., 2022, 87, 6638–6656.
DOI: 10.1021/acs.joc.2c00295

61. Formation of Breslow Intermediates from N-Heterocyclic Carbenes and Aldehydes Involves Autocatalysis by the Breslow Intermediate, and a Hemiacetal
A. Wessels, M. Klußmann, M. Breugst, N. E. Schlörer, A. Berkessel, Angew. Chem. Int. Ed., 2022, 61, e202117682; Angew. Chem., 2022, 132, e202117682.
DOI: 10.1002/anie.202117682
Selected as a Hot Paper.

60. Ammonium Pertechnetate in Mixtures of Trifluoromethanesulfonic Acid and Trifluoromethanesulfonic Anhydride
M. Zegke,* D. Grödler, M. Roca Jungfer, A. Haseloer, M. Kreuter, J. M. Neudörfl, T. Sittel, C. M. James, J. Rothe, M. Altmaier, A. Klein, M. Breugst,* U. Abram, E. Strub,* M. S. Wickleder,* Angew. Chem. Int. Ed., 2022, 61, e202113777; Angew. Chem., 2022, 134, e202113777.
DOI: 10.1002/anie.202113777
Selected as a Hot Paper.

59. Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
V. Pitchumani, M. Breugst, D. W. Lupton, Org. Lett., 2021, 23, 9413–9418.
DOI: 10.1021/acs.orglett.1c03554

58. Some Surprising Transformations of Colchicone and other Colchicine-derived Tropolones
A., P. Hilken nee Thomopoulou, T. Schulte, J.-M. Neudörfl, M. Breugst,* H.-G. Schmalz,* Eur. J. Org. Chem., 2021, 6375–6382.
DOI: 10.1002/ejoc.202100999
Selected as a VIP Paper.

57. Iodine‐Catalyzed Diels‐Alder Reactions
T. Arndt, P. K. Wagner, J. J. Koenig, M. Breugst,* ChemCatChem, 2021, 13, 2922–2930.
DOI: 10.1002/cctc.202100342
Invited contribution to the special collection Young Researchers Series

56. Catalysis by Molecular Iodine (Book Chapter)
J. J. König, M. Breugst,* in Halogen Bonding in Solution (Ed. S. M. Huber), 2021, 233–268.
DOI: 10.1002/9783527825738.ch7
ISBN (print): 978-3-527-34731-5

55. Breslow Intermediates (Aminoenols) and their Keto Tautomers: First Gas‐Phase Characterization by IR Ion Spectroscopy
M. Paul, K. Peckelsen, T. Thomulka, J. Martens, G. Berden, J. Oomens, J. M. Neudörfl, M. Breugst,* A. J. H. M. Meijer,* M. Schäfer,* A. Berkessel,* Chem. Eur. J., 2021, 27, 2662–2669.
DOI: 10.1002/chem.202003454
Selected as a VIP Paper

54. Enantioselective N-Heterocyclic Carbene Catalysis via the Acyl Azolium without Exogenous Oxidants
J. Cao, R. Gillard, A. Jahanbakhsh, M. Breugst, D. W. Lupton, ACS Catal., 2020, 10, 11791–11796.
DOI: 10.1021/acscatal.0c02705

53. Competition Between N and O: Use of Diazine N-Oxides as a Test Case for the Marcus Theory Rationale for Ambident Reactivity
K. Sheehy, L. M. Bateman, N. T. Flosbach, M. Breugst,* P. A. Byrne,* Chem. Sci., 2020, 11, 9630–9647.
DOI: 10.1039/D0SC02834G

52. Experimental and Computational Investigations of the Reaction between α,β‐unsaturated Lactones and 1,3‐Dienes by Cooperative Lewis‐Acid/Brønsted‐Acid Catalysis
A. Weber, M. Breugst,* J. Pietruszka,* Angew. Chem. Int. Ed., 2020, 59, 18709–18716; Angew. Chem., 2020, 132, 18868–18875.
DOI: 10.1002/anie.202008365

51. σ‐Hole Interactions in Catalysis
M. Breugst,* J. J. König, Eur. J. Org. Chem., 2020, 5473–5487.
DOI: 10.1002/ejoc.202000660
Selected as a VIP Paper. Also included in the virtual issue: Hot Topic: Organocatalysis

50. The Huisgen Reaction – Milestones of the 1,3-Dipolar Cycloaddition
M. Breugst,* H. Reißig,* Angew. Chem. Int. Ed., 2020, 59, 12293–12307; Angew. Chem., 2020, 132, 12389–12404.
DOI: 10.1002/anie.202003115
Also included in the virtual issues: Hot Topic: Click Chemistry and In memory of Rolf Huisgen

49. Unambiguous Identification of N- or O-Alkylation of Aromatic Nitrogen Heterocycles and N-Oxides Using 1H-15N HMBC NMR Spectroscopy
K. J. Sheehy, L. M. Bateman, N. T. Flosbach, M. Breugst,* P. A. Byrne,* Eur. J. Org. Chem., 2020, 3270–3281.
DOI: 10.1002/ejoc.202000329
Also included in the virtual issue: In memory of Rolf Huisgen

48. Synthesis of the 8,19‐Epoxysteroid Eurysterol A
Ö. Taspinar, T. Wilczek, J. Erver, M. Breugst, J.-M. Neudörfl, H.-G. Schmalz, Chem. Eur. J., 2020, 26, 4256–4260.
DOI: 10.1002/chem.202000585

47. Enantioselective Allylation of Indoles: A Surprising Diastereoselectivity
P. Ullrich, J. Schmauck, M. Brauns, M. Mantel, M. Breugst,* J. Pietruszka,* J. Org. Chem., 2020, 85, 1894–1905.
DOI: 10.1021/acs.joc.9b02573

46. The Technical Synthesis of 1,5,9-Cyclododecatriene Revisited: Surprising By-products from a Venerable Industrial Process
F. Thrun, V. Hickmann, C. Stock, A. Schaefer, W. Maier, M. Breugst, N. E. Schlörer, A. Berkessel, H. Teles, J. Org. Chem., 2019, 84, 13211–13220.
DOI: 10.1021/acs.joc.9b01633
Selected as a Featured Article.

45. N-Heterocyclic Carbene Catalyzed (5 + 1) Annulations Exploiting a Vinyl Dianion Synthon Strategy
X. B. Nguyen, Y. Nakano, N. M. Duggan, L. Scott, M. Breugst, D. W. Lupton, Angew. Chem. Int. Ed., 2019, 58, 11483–11490; Angew. Chem., 2019, 131, 11607–11614.
DOI: 10.1002/anie.201905475

44. Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities
R. J. Mayer, M. Breugst, N. Hampel, A. R. Ofial, H. Mayr, J. Org. Chem., 2019, 84, 8837–8858.
DOI: 10.1021/acs.joc.9b01485
Selected as a Featured Article.

43. Iodine-Catalyzed Nazarov Cyclizations
J. J. König, T. Arndt, N. Gildemeister, J.-M. Neudörfl, M. Breugst*, J. Org. Chem., 2019, 84, 7587–7605.
DOI: 10.1021/acs.joc.9b01083
Selected as a Featured Article.

42. Philicity of Acetonyl and Benzoyl Radicals: a Comparative Experimental and Computational Study
R. H. Verschueren, J. Schmauck, M. S. Perryman, H.-L. Yue, J. Riegger, B. Schweitzer-Chaput, M. Breugst,* M. Klussmann,* Chem. Eur. J., 2019, 25, 9088–9097.
DOI: 10.1002/chem.201901439
Selected as a Hot Paper.

41. Radical Addition of Ketones and Cyanide to Olefins via Acid Catalyzed Formation of Intermediate Alkenyl Peroxides
W. Shao, M. Lux, M. Breugst, M. Klussmann, Org. Chem. Front., 2019, 6, 1796–1800.
DOI: 10.1039/C9QO00447E

40. Intermediates of N‐Heterocyclic Carbene (NHC) Dimerization Probed in the Gas Phase by Ion Mobility Mass Spectrometry: C‐H⋯:C Hydrogen Bonding vs. Covalent Dimer Formation
M. Paul,* E. Detmar, M. Schlangen, M. Breugst,* J.-M. Neudörfl, H. Schwarz, A. Berkessel,* M. Schäfer,* Chem. Eur. J., 2019, 67, 2511–2518.
DOI: 10.1002/chem.201803641

39. Carbonyl-Olefin Metathesis Catalyzed by Molecular Iodine
U. P. N. Tran, G. Oss, M. Breugst, E. Detmar, D. P. Pace, K. Liyanto, T. V. Nguyen, ACS Catal., 2019, 9, 912–919.
DOI: 10.1021/acscatal.8b03769

38. Reaktionen im kontinuierlichen Strom
J. König, M. Breugst,* Nachr. Chem., 2019, 67, 81–85.
DOI: 10.1002/nadc.20194084228

37. Katalyse mit elektrophilen Phosphoniumionen
J. Schmauck, M. Breugst,* Nachr. Chem., 2018, 66, 862–865.
DOI: 10.1002/nadc.20184077309

36. Redetermination of the Solvent-Free Crystal Structure of L-Proline
J. J. König, J.-M. Neudörfl, A. Hansen, M. Breugst,* Acta Crystallogr., Sect. E: Crystallogr. Commun., 2018, E74, 1067–1070.
DOI: 10.1107/S2056989018009490

35. Visible Light–Mediated Metal–Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations
W. Lecroq, P. Bazille, F. Morlet-Savary, J. Lalevée, M. Breugst,* A.-C. Gaumont, S. Lakhdar,* Org. Lett., 2018, 20, 4164–4167.
DOI: 10.1021/acs.orglett.8b01379
selected for the Organic Letters Global Enterprise Virtual Issue
highlighted on www.organic-chemistry.org: link

34. Cobalt-Catalyzed C–H Cyanations: Insights into the Reaction Mechanism and the Role of London Dispersion
E. Detmar, V. Müller, D. Zell, L. Ackermann,* M. Breugst,* Beilstein J. Org. Chem., 2018, 14, 1537–1545.
DOI: 10.3762/bjoc.14.130
Invited contribution to the Thematic Series Dispersion interactions.

33. Sperrige Substituenten – Zwischen Attraktion und Repulsion
J. J. König, M. Breugst,* Nachr. Chem., 2018, 66, 505–509.
DOI: 10.1002/nadc.20184073225

32. Regioselective 1,3-Dipolar Cycloadditions of Diazoalkanes with Heteroatom-Substituted Alkynes: Theory and Experiment
M. Breugst,* R. Huisgen, H.-U. Reissig,* Eur. J. Org. Chem., 2018, 2477–2485.
DOI: 10.1002/ejoc.201800100
invited contribution for the 20^th Anniversary (Celebrating the Past, Present and Future)
highlighted in a ChemViews Magazine interview with the authors

31. Mechanisms in Iodine Catalysis
M. Breugst,* D. von der Heiden, Chem. Eur. J., 2018, 24, 9187–9199.
DOI: 10.1002/chem.201706136
Selected by the Editorial Office for the Showcase of outstanding Review-type articles.

30. Activation of Michael Acceptors by Halogen-Bond Donors
D. von der Heiden, E. Detmar, R. Kuchta, M. Breugst,* Synlett, 2018, 1307–1313.
DOI: 10.1055/s-0036-1591841
invited contribution for the Special Section 9^th EuCheMS Organic Division Young Investigator Workshop

29. The potential of pnicogen bonding for catalysis – A computational study
J. Schmauck, M. Breugst,* Org. Biomol. Chem., 2017, 15, 8037–8045.
DOI: 10.1039/C7OB01599B

28. Kinetics of Electrophilic Alkylations of Barbiturate and Thiobarbiturate Anions
A. Schade, I. Tchernook, M. Bauer, A. Oehlke, M. Breugst, J. Friedrich, S. Spange, J. Org. Chem., 2017, 82, 8476–8488.
DOI: 10.1021/acs.joc.7b01223

27. Novel Noncovalent Interactions in Catalysis: A Focus on Halogen, Chalcogen, and Anion-π Bonding
M. Breugst,* D. von der Heiden, J. Schmauck, Synthesis, 2017, 49, 3224–3236.
DOI: 10.1055/s-0036-1588838

26. Highly Enantioselective Allylation of Ketones - An Efficient Approach to all Stereoisomers of Tertiary Homoallylic Alcohols
M. Brauns, M. Mantel, J. Schmauck, M. Guder, M. Breugst,* J. Pietruszka,* Chem. Eur. J., 2017, 23, 12136–12140.
DOI: 10.1002/chem.201701740

25. Reaction Mechanism of Iodine-Catalyzed Michael Additions
D. von der Heiden, S. Bozkus, M. Klussmann, M. Breugst,* J. Org. Chem. 2017, 82, 4037–4043.
DOI: 10.1021/acs.joc.7b00445
Selected as a Featured Article.

24. A Metal–Free Synthesis of 6–Phosphorylated Phenanthridines: Synthetic and Mechanistic Insights
L. Noël-Duchesneau, E. Lagadic, F. Morlet-Savary, J.-F. Lohier, I. Chataigner, M. Breugst,* J. Lalevée, A.-C. Gaumont, S. Lakhdar,* Org. Lett. 2016, 18, 5900–5903.
DOI: 10.1021/acs.orglett.6b02983
Highlighted in Synfacts 2017, 13, 140.

23. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization
L. Ma, A. Paul, M. Breugst,* D. Seidel,* Chem. Eur. J. 2016, 22, 18179–18189.
DOI: 10.1002/chem.201603839

22. Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes
A. Levens, F. An, M. Breugst, H. Mayr, D. W. Lupton, Org. Lett. 2016, 18, 3566–3569.
DOI: 10.1021/acs.orglett.6b01525

21. Origin of the Catalytic Effects of Molecular Iodine – A Computational Analysis
M. Breugst,* E. Detmar, D. von der Heiden, ACS Catal. 2016, 6, 3203–3212.
DOI: 10.1021/acscatal.6b00447

20. Quantification of the Nucleophilic Reactivity of Nicotine
P. A. Byrne, S. Kobayashi, M. Breugst, H. Laub, H. Mayr, J. Phys. Org. Chem. 2016, 29, 759–767.
DOI: 10.1002/poc.3580

19. Keto-Enol Thermodynamics of Breslow Intermediates
M. Paul, M. Breugst, J.-M. Neudörfl, R. B. Sunoj, A. Berkessel, J. Am. Chem. Soc. 2016, 138, 5044–5051.
DOI: 10.1021/jacs.5b13236

18. Enantioselective Catalysts for the Synthesis of α-Substituted Allyboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols
M. Brauns, F. Muller, D. Gülden, D. Böse, W. Frey, M. Breugst,* J. Pietruszka,* Angew. Chem. Int. Ed. 2016, 55, 1548–1552; Angew. Chem. 2016, 128, 1574–1578.
DOI: 10.1002/anie.201509198

17. Mit molekularem Iod katalysieren
M. Breugst, Nachr. Chem. 2015, 63, 1180–1183.
DOI: 10.1002/nadc.201590404

16. Asymmetric Redox-Annulation of Cyclic Amines
Y. Kang, W. Chen, M. Breugst,* D. Seidel,* J. Org. Chem. 2015, 80, 9628–9640.
DOI: 10.1021/acs.joc.5b01384

15. Experimental and Computational Studies on the C-H Amination Mechanism of Tetrahydrocarbazoles via Hydroperoxides
N. Gulzar, K. M. Jones, H. Konnerth, M. Breugst,* M. Klussmann,* Chem. Eur. J. 2015, 21, 3367–3376.
DOI: 10.1002/chem.201405376

14. Computational Analysis of Cyclophane-Based Bisthiourea-Catalyzed Henry Reactions
M. Breugst,* K. N. Houk* J. Org. Chem. 2014, 79, 6302–6309.
DOI: 10.1021/jo501227m

13. Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
C. L. Jarvis, M. T. Richers, M. Breugst, K. N. Houk, D. Seidel, Org. Lett. 2014, 16, 3556–3559.
DOI: 10.1021/ol501509b

12. Redox-Neutral α-Oxygenation of Amines: Reaction Development and Elucidation of the Mechanism
M. T. Richers, M. Breugst, A. Y. Platonova, A. Ullrich, A. Dieckmann, K. N. Houk, D. Seidel, J. Am. Chem. Soc. 2014, 136, 6123–6135.
DOI: 10.1021/ja501988b

11. δ-Deuterium Isotope Effects as Probes for Transition State Structures of Isoprenoid Substrates
S.-r. Choi, M. Breugst, K. N. Houk, C. D. Poulter, J. Org. Chem. 2014, 79, 3572–3580.
DOI: 10.1021/jo500394u

10. Synergistic Effects Between Lewis and Brønsted Acids – Application to the Prins Cyclization
M. Breugst,* R. Grée, K. N. Houk,* J. Org. Chem. 2013, 78, 9892–9897.
DOI: 10.1021/jo401628e

09. Theoretical Exploration of the Mechanism of Riboflavin Formation from 6,7-Dimethyl-8-ribityl-lumazine: Hydride Transfer, Hydrogen Atom Transfer, Nucleophilic Addition, or Nucleophilic Catalysis?
M. Breugst, A. Eschenmoser, K. N. Houk, J. Am. Chem. Soc. 2013, 135, 6658–6668.
DOI: 10.1021/ja402099f

08. Zwitterions and Unobserved Intermediates in Organocatalytic Diels-Alder Reactions of Linear and Cross-Conjugated Trienamines
A. Dieckmann, M. Breugst, K. N. Houk, J. Am. Chem. Soc. 2013, 135, 3237–3242.
DOI: 10.1021/ja312043g
Highlighted in Comp. Chem. Highlights, 2013, 2013.04.zwitterions.

07. Nucleophilic Reactivities of the Anions of Nucleobases and Their Subunits
M. Breugst, F. Corral Bautista, H. Mayr, Chem. Eur. J. 2012, 18, 127–137.
DOI: 10.1002/chem.201102411
Selected as a VIP Paper.

06. N-Heterocyclic Carbenes: Organocatalysts with Moderate Nucleophilicity but Extraordinarily High Lewis Basicity
B. Maji, M. Breugst, H. Mayr, Angew. Chem. Int. Ed. 2011, 50, 6915–6919; Angew. Chem. 2011, 123, 7047–7052.
DOI: 10.1002/anie.201102435

05. Farewell to the HSAB Treatment of Ambident Reactivity
H. Mayr, M. Breugst, A. R. Ofial, Angew. Chem. Int. Ed. 2011, 50, 6470–6505; Angew. Chem. 2011, 123, 6598–6634.
DOI: 10.1002/anie.201007100

04. Ambident Reactivities of Pyridone Anions
M. Breugst, H. Mayr, J. Am. Chem. Soc. 2010, 132, 15380–15389.
DOI: 10.1021/ja106962u

03. Nucleophilic Reactivities of Imide and Amide Anions
M. Breugst, T. Tokuyasu, H. Mayr, J. Org. Chem. 2010, 75, 5050–5258.
DOI: 10.1021/jo1009883

02. Marcus-Analysis of Ambident Reactivity
M. Breugst, H. Zipse, J. P. Guthrie, H. Mayr, Angew. Chem. Int. Ed. 2010, 49, 5165–5169; Angew. Chem. 2010, 122, 5291–5295. DOI: 10.1002/anie.201001574

01. Towards a General Scale of Nucleophilicity?
T. B. Phan, M. Breugst, H. Mayr, Angew. Chem. Int. Ed. 2006, 45, 3869–3874; Angew. Chem. 2006, 118, 3954–3959.
DOI: 10.1002/anie.200600542
Selected as a VIP Paper.