Recyclable Palladium Catalyst for Highly Selective α Alkylation of Ketones with Alcohols†
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) 54-279-3399
Search for more papers by this authorNamdu 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) 54-279-3399
Search for more papers by this authorSeong 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) 54-279-3399
Search for more papers by this authorIn 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) 54-279-3399
Search for more papers by this authorRavi 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) 54-279-3399
Search for more papers by this authorJaiwook Park Prof.
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) 54-279-3399
Search for more papers by this authorMin 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) 54-279-3399
Search for more papers by this authorNamdu 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) 54-279-3399
Search for more papers by this authorSeong 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) 54-279-3399
Search for more papers by this authorIn 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) 54-279-3399
Search for more papers by this authorRavi 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) 54-279-3399
Search for more papers by this authorJaiwook Park Prof.
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) 54-279-3399
Search for more papers by this authorThis work was supported by the SRC/ERC program of MOST/KOSEF (R11-2000-070-05003-0).
Graphical Abstract
An air-stable, heterogeneous, and recyclable catalyst composed of palladium nanoparticles entrapped in aluminum hydroxide was applied to a highly selective α alkylation. A wide range of aliphatic and aromatic ketones and primary alcohols were coupled to prepare enones in an O2 atmosphere and ketones in an argon atmosphere (see scheme).
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/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.
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- 8According to 1H NMR spectroscopic analysis, no diastereomer of the major coupling product was formed in significant yield.
- 9Palladium was not detected in the filtrate with inductively coupled plasma (ICP) analysis.
- 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.
