Title: Palladium‐Catalyzed Dehydrogenative β′‐Arylation of β‐Keto Esters under Aerobic Conditions: Interplay of Metal and Brønsted Acids
Abstract: Chemistry – A European JournalVolume 18, Issue 40 p. 12590-12594 Communication Palladium-Catalyzed Dehydrogenative β′-Arylation of β-Keto Esters under Aerobic Conditions: Interplay of Metal and Brønsted Acids Kai-Tai Yip, Kai-Tai Yip Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorRoshan Y. Nimje, Roshan Y. Nimje Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorMikko V. Leskinen, Mikko V. Leskinen Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorPetri M. Pihko, Corresponding Author Petri M. Pihko [email protected] Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this author Kai-Tai Yip, Kai-Tai Yip Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorRoshan Y. Nimje, Roshan Y. Nimje Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorMikko V. Leskinen, Mikko V. Leskinen Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this authorPetri M. Pihko, Corresponding Author Petri M. Pihko [email protected] Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Department of Chemistry and Nanoscience Center, University of Jyväskylä, P. O. B. 35, F40014 JYU (Finland)Search for more papers by this author First published: 22 August 2012 https://doi.org/10.1002/chem.201201988Citations: 38Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The Brønsted aids: The first dehydrogenative arylation of β-keto esters with arenes under ambient aerobic conditions is described (see scheme). Under a PdII/Brønsted acid co-catalytic system, regioselective arylations with alkoxylated arenes and phenols were achieved in good yields, even in gram-scale conditions. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201201988_sm_miscellaneous_information.pdf3.4 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1For recent reviews on dehydrogenative cross-coupling, see: 1aC. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215; 1bC. J. Scheuermann, Chem. Asian J. 2010, 5, 436; 1cC.-J. Li, Acc. Chem. 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Chem. Int. Ed. 2004, 43, 6144. 3For an overview, see: 3aJ. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359. For arenes, see: 3bY. Rong, W. Lu, Organometallics 2007, 26, 4376; 3cK. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047; for phenolic compounds, see: 3dH. Egami, T. Katsuki, J. Am. Chem. Soc. 2009, 131, 6082; 3eX. Li, B. Hewgley, C. A. Mulrooney, J. Yang, M. C. Kozlowski, J. Org. Chem. 2003, 68, 5500; 3fA. S. Hay, H. S. Blanchard, G. F. Endres, J. W. Eustance, J. Am. Chem. Soc. 1959, 81, 6335; 3gH. Finkbeiner, A. S. Hay, H. S. Blanchard, G. F. Endres, J. Org. Chem. 1966, 31, 549. 4For selected examples of dehydrogenative heterocoupling with regiocontrol, see: 4aT. W. Lyons, K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 4455; 4bH. Egami, K. Matsumoto, T. Oguma, T. Kunisu, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 13633; 4cD. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072; 4dK. L. Hull, M. S. 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Baudoin, Chem. Eur. J. 2012, 18, 1932. 7M. V. Leskinen, K.-T. Yip, A. Valkonen, P. M. Pihko, J. Am. Chem. Soc. 2012, 134, 5750. 8For recent reviews, see: 8aA. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851; 8bZ. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381; 8cT. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329; 8dS. S. Stahl, Angew. Chem. 2004, 116, 3480; Angew. Chem. Int. Ed. 2004, 43, 3400. 9For a pioneering study on the effect of acidic medium on PdII-catalyzed arene functionalization reactions, see: 9aC. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633; 9bC. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992. 10See the Supporting Information for detailed screens. 11 11aX. Guo, R. Yu, H. Li, Z. Li, J. Am. Chem. Soc. 2009, 131, 17387; 11bK. M. Bogle, D. J. Hirst, D. J. Dixon, Org. Lett. 2007, 9, 4901; 11cR. B. Bedford, S. J. Coles, M. B. Hursthouse, M. E. Limmert, Angew. Chem. 2003, 115, 116; Angew. Chem. Int. Ed. 2003, 42, 112; 11dK. Kobayashi, M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 8528. 12See Supporting Information for details. 13It should be noted that the "early- and late-arylation" pathways are not necessarily exclusive. 14Due to the instability of enone derived from 1 a and the proton–deuterium exchange of arene 2 a in [D4]acetic acid, the kinetics of enone formation experiments and dehydrogenative couplings were studied under slightly different, but comparable conditions. 15Detailed studies and the mechanistic implications of the accelerated effect of dehydrogenation of 1 a will be reported in due course. 16These reactions would take place via oxidative addition pathways, as in reference [6]. 17CCDC-879905 (3 a) and CCDC-880392 (3 v) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Volume18, Issue40October 1, 2012Pages 12590-12594 ReferencesRelatedInformation
Publication Year: 2012
Publication Date: 2012-08-22
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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