Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones.
DDQ
Enol-Catalysis
Oxidations
Phosphoric Acids
α,β-Unsaturated Ketones
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
28 Aug 2023
28 Aug 2023
Historique:
received:
19
05
2023
medline:
20
6
2023
pubmed:
20
6
2023
entrez:
20
6
2023
Statut:
ppublish
Résumé
We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.
Identifiants
pubmed: 37337974
doi: 10.1002/anie.202307081
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202307081Subventions
Organisme : H2020 European Research Council
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
S. Gnaim, J. C. Vantourout, F. Serpier, P.-G. Echeverria, P. S. Baran, ACS Catal. 2021, 11, 883-892.
T. Mukaiyama, J.-I. Matsuo, H. Kitagawa, Chem. Lett. 2000, 29, 1250-1251.
Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013.
B. M. Trost, T. N. Salzmann, K. Hiroi, J. Am. Chem. Soc. 1976, 98, 4887-4902.
H. J. Reich, I. L. Reich, J. M. Renga, J. Am. Chem. Soc. 1973, 95, 5813-5815.
S. Gnaim, Y. Takahira, H. R. Wilke, Z. Yao, J. Li, D. Delbrayelle, P. G. Echeverria, J. C. Vantourout, P. S. Baran, Nat. Chem. 2021, 13, 367-372.
R. C. Larock, T. R. Hightower, G. A. Kraus, P. Hahn, D. Zheng, Tetrahedron Lett. 1995, 36, 2423-2426.
T. Diao, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 14566-14569.
D. Huang, Y. Zhao, T. R. Newhouse, Org. Lett. 2018, 20, 684-687.
X. W. Zhang, G. Q. Jiang, S. H. Lei, X. H. Shan, J. P. Qu, Y. B. Kang, Org. Lett. 2021, 23, 1611-1615.
K. C. Nicolaou, Y. L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597.
M. Schittmayer, A. Glieder, M. K. Uhl, A. Winkler, S. Zach, J. H. Schrittwieser, W. Kroutil, P. Macheroux, K. Gruber, S. Kambourakis, J. D. Rozzell, M. Winkler, Adv. Synth. Catal. 2011, 353, 268-274.
G. Pousse, F. Le Cavelier, L. Humphreys, J. Rouden, J. Blanchet, Org. Lett. 2010, 12, 3582-3585.
B. List, G. Shevchenko, S. Dehn, Synlett 2018, 29, 2298-2300.
B. List, G. Shevchenko, G. Pupo, Synlett 2015, 26, 1413-1416.
G. Pupo, R. Properzi, B. List, Angew. Chem. Int. Ed. 2016, 55, 6099-6102.
G. A. Shevchenko, B. Oppelaar, B. List, Angew. Chem. Int. Ed. 2018, 57, 10756-10759.
X. Yang, F. D. Toste, J. Am. Chem. Soc. 2015, 137, 3205-3208.
M. Schmittel, A. Abufarag, O. Luche, M. Levis, Angew. Chem. Int. Ed. 1990, 29, 1144-1146.
M. Schmittel, M. Lal, R. Lal, M. Röck, A. Langels, Z. Rappoport, A. Basheer, J. Schlirf, H.-J. Deiseroth, U. Flörke, G. Gescheidt, Tetrahedron 2009, 65, 10842-10855.
A. Bhattacharya, L. M. DiMichele, U. H. Dolling, E. J. J. Grabowski, V. J. Grenda, J. Org. Chem. 1989, 54, 6118-6120.
A. E. Wendlandt, S. S. Stahl, Angew. Chem. Int. Ed. 2015, 54, 14638-14658.
I. Ryu, S. Murai, Y. Hatayama, N. Sonoda, Tetrahedron Lett. 1978, 19, 3455-3458.
M. A. Alsharif, Q. A. Raja, N. A. Majeed, R. S. Jassas, A. A. Alsimaree, A. Sadiq, N. Naeem, E. U. Mughal, R. I. Alsantali, Z. Moussa, S. A. Ahmed, RSC Adv. 2021, 11, 29826-29858.
J. Blom, G. J. Reyes-Rodriguez, H. N. Tobiesen, J. N. Lamhauge, M. V. Iversen, C. L. Barlose, N. Hammer, M. Rusbjerg, K. A. Jørgensen, Angew. Chem. Int. Ed. 2019, 58, 17856-17862.
H. Künzer, M. Stahnke, G. Sauer, R. Wiechert, Tetrahedron Lett. 1990, 31, 3859-3862.
L. Simón, J. M. Goodman, J. Am. Chem. Soc. 2008, 130, 8741-8747.
X. Guo, H. Mayr, J. Am. Chem. Soc. 2013, 135, 12377-12387.