zum Inhalt springen

2020

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., 2020, 26, EarlyView.
DOI: 10.1002/chem.202003454

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

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

Publikation 34

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".

Publikation 33

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.

2012

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.

2011

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

Older Publications

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.