2022
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.
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, e202113777.
DOI: 10.1002/anie.202113777
Selected as a Hot Paper.
2021
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.
2020
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., 2020, 132, 18868–18875; Angew. Chem. Int. Ed., 2020, 59, 18709–18716.
DOI (English Version): 10.1002/anie.202008365
DOI (Deutsche Fassung): 10.1002/ange.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
50. Die Huisgen-Reaktion – Meilensteine der 1,3-Dipolaren Cycloaddition
M. Breugst,* H. Reißig,* Angew. Chem., 2020, 132, 12389–12404; Angew. Chem. Int. Ed., 2020, 59, 12293–12307.
DOI (English Version): 10.1002/anie.202003115
DOI (Deutsche Fassung): 10.1002/ange.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
2019
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., 2019, 131, 11607–11614; Angew. Chem. Int. Ed., 2019, 58, 11483–11490.
DOI (English Version): 10.1002/anie.201905475
DOI (Deutsche Fassung): 10.1002/ange.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
most read article in ACS Catalysis in January and February 2019
38. Reaktionen im kontinuierlichen Strom
J. König, M. Breugst,* Nachr. Chem., 2019, 67, 81–85.
DOI: 10.1002/nadc.20194084228
2018
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
DOI (Cover): 10.1002/ejoc.201800739
invited contribution for the 20th 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 (English Version): 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 (English Version): 10.1055/s-0036-1591841
invited contribution for the Special Section 9th EuCheMS Organic Division Young Investigator Workshop
2017
29. The potential of pnicogen bonding for catalysis – A computational study
J. Schmauck, M. Breugst,* Org. Biomol. Chem., 2017, 15, 8037–8045.
DOI (English Version): 10.1039/C7OB01599B
DOI (Cover): 10.1039/C7OB90160G
invited contribution for the themed collection Mechanistic Aspects of Organic Synthesis
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 (English Version): 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 (English Version): 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 (English Version): 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 (English Version): 10.1021/acs.joc.7b00445
Selected as a Featured Article.
2016
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 (English Version): 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 (English Version) 10.1002/chem.201603839
Selected as a Hot Paper.
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 (English Version) 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 (English Version) 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 (English Version) 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 (English Version) 10.1021/jacs.5b13236
18. Enantioselective Catalysts for the Synthesis of α-Substituted Allyboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols
18. Enantioselektive Katalysatoren zur Synthese von α-substituierten Allylboronsäureestern - ein effizienter Zugang zu isomerenreinen Homoallylalkoholen
M. Brauns, F. Muller, D. Gülden, D. Böse, W. Frey, M. Breugst,* J. Pietruszka* Angew. Chem. 2016, 128, 1574–1578; Angew. Chem. Int. Ed. 2016, 55, 1548–1552.
DOI (Deutsche Fassung) 10.1002/ange.201509198
DOI (English Version) 10.1002/anie.201509198
2015
17. Mit molekularem Iod katalysieren
M. Breugst Nachr. Chem. 2015, 63, 1180–1183.
DOI (Deutsche Version) 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 (English Version) 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 (English Version) 10.1002/chem.201405376
2014
14. Computational Analysis of Cyclophane-Based Bisthiourea-Catalyzed Henry Reactions
M. Breugst,* K. N. Houk* J. Org. Chem. 2014, 79, 6302–6309.
DOI (English Version) 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 (English Version) 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 (English Version) 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 (English Version) 10.1021/jo500394u
2013
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 (English Version) 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 (English Version) 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.
Older Publications
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
06. N-Heterocyclische Carbene: Organokatalysatoren mit mäßiger Nucleophilie, aber außerordentlich hoher Lewis-Basizität
B. Maji, M. Breugst, H. Mayr, Angew. Chem. 2011, 123, 7047–7052; Angew. Chem. Int. Ed. 2011, 50, 6915–6919.
DOI (Deutsche Fassung) 10.1002/ange.201102435
DOI (English Version) 10.1002/anie.201102435
05. Farewell to the HSAB Treatment of Ambident Reactivity
05. Abschied vom HSAB-Modell ambidenter Reaktivität
H. Mayr, M. Breugst, A. R. Ofial, Angew. Chem. 2011, 123, 6598–6634; Angew. Chem. Int. Ed. 2011, 50, 6470–6505.
DOI (Deutsche Fassung) 10.1002/ange.201007100
DOI (English Version) 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
02. Marcus-Analyse ambidenter Reaktivität
M. Breugst, H. Zipse, J. P. Guthrie, H. Mayr, Angew. Chem. 2010, 122, 5291–5295; Angew. Chem. Int. Ed. 2010, 49, 5165–5169.
DOI (Deutsche Fassung) 10.1002/ange.201001574
DOI (English Version) 10.1002/anie.201001574
01. Towards a General Scale of Nucleophilicity?
01. Auf dem Weg zu einer allgemeinen Nucleophilie-Skala?
T. B. Phan, M. Breugst, H. Mayr, Angew. Chem. 2006, 118, 3954–3959; Angew. Chem. Int. Ed. 2006, 45, 3869–3874.
DOI (Deutsche Fassung) 10.1002/ange.200600542
DOI (English Version) 10.1002/anie.200600542
Selected as a VIP Paper.