Cascade Carbonylation Methods Leading to β‐Diketones and β‐Functionalized δ‐Diketones
2004; Wiley; Volume: 43; Issue: 18 Linguagem: Inglês
10.1002/anie.200453702
ISSN1521-3773
AutoresKatsukiyo Miura, Mami Tojino, Naoki Fujisawa, Akíra Hosomi, Ilhyong Ryu,
Tópico(s)Sulfur-Based Synthesis Techniques
ResumoAngewandte Chemie International EditionVolume 43, Issue 18 p. 2423-2425 Communication Cascade Carbonylation Methods Leading to β-Diketones and β-Functionalized δ-Diketones† Katsukiyo Miura Dr., Katsukiyo Miura Dr. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorMami Tojino, Mami Tojino Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9695Search for more papers by this authorNaoki Fujisawa, Naoki Fujisawa Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorAkira Hosomi Prof., Akira Hosomi Prof. [email protected] Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorIlhyong Ryu Prof., Ilhyong Ryu Prof. [email protected] Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9695Search for more papers by this author Katsukiyo Miura Dr., Katsukiyo Miura Dr. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorMami Tojino, Mami Tojino Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9695Search for more papers by this authorNaoki Fujisawa, Naoki Fujisawa Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorAkira Hosomi Prof., Akira Hosomi Prof. [email protected] Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Fax: (+81) 298-53-4237Search for more papers by this authorIlhyong Ryu Prof., Ilhyong Ryu Prof. [email protected] Department of Chemistry, Faculty of Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan, Fax: (+81) 72-254-9695Search for more papers by this author First published: 22 April 2004 https://doi.org/10.1002/anie.200453702Citations: 46 † This work was supported by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science, and Technology, Government of Japan. A.H. acknowledges support from CREST, Science and Technology Corporation (JST). Read 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 Graphical Abstract A radical combination: An intermolecular cascade reaction involving alkyl halides, CO, electron-deficient alkenes, and stannyl enolates proceeds smoothly by a radical chain pathway to give four-component coupling products in good to high yields (see scheme). A series of 1,5-diketones with a substituent at the 3-position was prepared by this method. References 1For reviews on radical chemistry, see: 1a Radicals in Organic Synthesis, Vols. 1 and 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001; 1bD. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996; 1cW. B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic, London, 1992. 2For reviews on radical cascade reactions, see: 2aM. Malacria, Chem. Rev. 1996, 96, 289; 2bI. Ryu, N. Sonoda, D. P. Curran, Chem. Rev. 1996, 96, 177. 3For recent work on the use of tin enolates in radical reactions, see: 3aK. Miura, N. Fujisawa, H. Saito, D. Wang, A. Hosomi, Org. Lett. 2001, 3, 2591; 3bK. Miura, H. Saito, N. Fujisawa, D. Wang, H. Nishikori, A. Hosomi, Org. Lett. 2001, 3, 4055; for earlier work, see: 3cG. A. Russel, L. L. Herold, J. Org. Chem. 1985, 50, 1037; 3dY. Watanabe, T. Yoneda, Y. Ueno, T. Toru, Tetrahedron Lett. 1990, 31, 6669. 4For reviews on acyl radicals and radical carbonylations, see: 4aI. Ryu, N. Sonoda, Angew. Chem. 1996, 108, 1140; Angew. Chem. Int. Ed. Engl. 1996, 35, 1050; 4bI. Ryu, Chem. Soc. Rev. 2001, 30, 16; 4cC. Chatgilialoglu, D. Crich, M. Komatsu, I. Ryu, Chem. Rev. 1999, 99, 1991; Also see recent work: 4dI. Ryu, H. Miyazato, H. Kuriyama, K. Matsu, M. Tojino, T. Fukuyama, S. Minakata, M. Komatsu, J. Am. Chem. Soc. 2003, 125, 5632; 4eI. Ryu, S. Kreimerman, F. Araki, S. Nishitani, Y. Oderaotoshi, S. Minakata, M. Komatsu, J. Am. Chem. Soc. 2002, 124, 3813. 5For the related SH2′ reactions with allyltin compounds, see: 5aI. Ryu, H. Yamazaki, K. Kusano, A. Ogawa, N. Sonoda, J. Am. Chem. Soc. 1991, 113, 8558; 5bI. Ryu, H. Yamazaki, A. Ogawa, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 1187; 5cI. Ryu, T. Niguma, S. Minakata, M. Komatsu, Z. Luo, D. P. Curran, Tetrahedron Lett. 1999, 40, 2367. 6 6aY. Yamamoto, H. Yatagai, K. Maruyama, J. Chem. Soc. Chem. Commun. 1981, 162; 6bS. Shenvi, J. K. Stille, Tetrahedron Lett. 1982, 23, 627; 6cK. Kobayashi, M. Kawanishi, T. Hitomi, S. Kozima, Chem. Lett. 1983, 851. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53702_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. Volume43, Issue18April 26, 2004Pages 2423-2425 ReferencesRelatedInformation
Referência(s)