Rhodium‐Catalyzed Aryl Transfer from Trisubstituted Aryl Methanols to α,β‐Unsaturated Carbonyl Compounds
2007; Wiley; Volume: 46; Issue: 26 Linguagem: Inglês
10.1002/anie.200700902
ISSN1521-3773
AutoresTakahiro Nishimura, Taisuke Katoh, Tamio Hayashi,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoAngewandte Chemie International EditionVolume 46, Issue 26 p. 4937-4939 Communication Rhodium-Catalyzed Aryl Transfer from Trisubstituted Aryl Methanols to α,β-Unsaturated Carbonyl Compounds† Takahiro Nishimura Dr., Takahiro Nishimura Dr. [email protected] Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this authorTaisuke Katoh, Taisuke Katoh Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this authorTamio Hayashi Prof., Tamio Hayashi Prof. [email protected] Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this author Takahiro Nishimura Dr., Takahiro Nishimura Dr. [email protected] Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this authorTaisuke Katoh, Taisuke Katoh Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this authorTamio Hayashi Prof., Tamio Hayashi Prof. [email protected] Department of Chemistry, Graduate School of Science, Sakyo, Kyoto 606-8502, Japan, Fax: (+81) 75-753-3988Search for more papers by this author First published: 15 June 2007 https://doi.org/10.1002/anie.200700902Citations: 57 † This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan (Priority Areas "Advanced Molecular Transformations of Carbon Resources"). 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A process of elimination: The rhodium-catalyzed arylation of α,β-unsaturated carbonyl compounds with 9-aryl-10-benzyl-9,10-dihydroacridin-9-ols 1 as arylating reagents proceeds efficiently via β-aryl elimination of the rhodium alkoxide intermediates, to give the 1,4-addition products in high yields (see scheme; Bn=benzyl, cod=cycloocta-1,5-diene). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z700902_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 1aK. Yoshida, T. Hayashi in Modern Rhodium-Catalyzed Organic Reactions (Ed.: ), Wiley-VCH, Weinheim, 2005, chap. 3; Google Scholar 1bT. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829; 10.1021/cr020022z CASPubMedWeb of Science®Google Scholar 1cT. Hayashi, Bull. Chem. Soc. Jpn. 2004, 77, 13; 10.1246/bcsj.77.13 CASWeb of Science®Google Scholar 1dT. Hayashi, Pure Appl. Chem. 2004, 76, 465; 10.1351/pac200476030465 CASWeb of Science®Google Scholar 1eS. Darses, J.-P. Genet, Eur. J. Org. Chem. 2003, 4313; 10.1002/ejoc.200300294 CASWeb of Science®Google Scholar 1fK. 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