Title: Recyclable Palladium Catalyst for Highly Selective α Alkylation of Ketones with Alcohols
Abstract: Angewandte ChemieVolume 117, Issue 42 p. 7073-7075 Zuschrift Recyclable Palladium Catalyst for Highly Selective α Alkylation of Ketones with Alcohols† Min Serk Kwon, Min Serk Kwon Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorNamdu Kim, Namdu Kim Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorSeong Hyeok Seo, Seong Hyeok Seo Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorIn Soo Park, In Soo Park Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorRavi Kumar Cheedrala, Ravi Kumar Cheedrala Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorJaiwook Park Prof., Jaiwook Park Prof. [email protected] Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this author Min Serk Kwon, Min Serk Kwon Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorNamdu Kim, Namdu Kim Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorSeong Hyeok Seo, Seong Hyeok Seo Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorIn Soo Park, In Soo Park Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorRavi Kumar Cheedrala, Ravi Kumar Cheedrala Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this authorJaiwook Park Prof., Jaiwook Park Prof. [email protected] Center for Integrated Molecular Systems, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology (POSTECH), San 31 Hyoja Dong, Pohang 790-784, Korea, Fax: (+82) 54-279-3399Search for more papers by this author First published: 25 October 2005 https://doi.org/10.1002/ange.200502422Citations: 62 † This work was supported by the SRC/ERC program of MOST/KOSEF (R11-2000-070-05003-0). Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 Luftbeständig und wiederverwendbar ist ein Heterogenkatalysator aus Palladium-Nanopartikeln in einer Aluminiumhydroxidmatrix. Die hoch selektive α-Alkylierung von aliphatischen und aromatischen Ketonen mit primären Alkoholen führte in einer O2-Atmosphäre zu Enonen und in einer Argonatmosphäre zu Ketonen (siehe Schema). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2005/z502422_s.pdf or from the author. 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 1 1aD. Caine in Comprehensive Organic Synthesis, Vol. 3 (Eds.: ), Pergamon, Oxford, 1991, pp. 1–63; Google Scholar 1bS. Carrettin, J. Guzman, A. Corma, Angew. Chem. 2005, 117, 2282–2285; 10.1002/ange.200462560 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 2242–2245; 10.1002/anie.200462560 CASPubMedWeb of Science®Google Scholar 1c Modern Carbonyl Chemistry (Ed.: ), Wiley-VCH, Weinheim, 2000. Google Scholar 2 2aC. S. Cho, B. T. Kim, M. J. Lee, T.-J. Kim, S. C. Shim, Angew. 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Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 5662–5663. 10.1021/ja049181l CASPubMedWeb of Science®Google Scholar 4M. S. Kwon, N. Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077–1079. 10.1021/ol047381w CASPubMedWeb of Science®Google Scholar 5The coupling reaction was completed in 16 h (10 h) when one equivalent (2 equiv) of K3PO4 was used. Google Scholar 6The major product is the corresponding alcohol when [Ru(dmso)4]Cl2 is used as the catalyst; see ref. [2f]. Google Scholar 7Pregnenolone is a main precursor of steroid hormones: K. Tsutsui, H. Sakamoto, K. Ukena, J. Steroid Biochem. Mol. Biol. 2003, 85, 311–321. 10.1016/S0960-0760(03)00229-2 CASPubMedWeb of Science®Google Scholar 8According to 1H NMR spectroscopic analysis, no diastereomer of the major coupling product was formed in significant yield. Google Scholar 9Palladium was not detected in the filtrate with inductively coupled plasma (ICP) analysis. Google Scholar 10The NMR spectroscopic data for the coupling products shown in Table 3 and the experimental procedures for the preparation of 1, E-1,3-diphenyl-2-propen-1-one, and 21-benzylpregnenolone are contained in the Supporting Information. Google Scholar Citing Literature Volume117, Issue42October 28, 2005Pages 7073-7075 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Publication Year: 2005
Publication Date: 2005-10-05
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 62
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