Tin‐Free Radical Allylation of B ‐Alkylcatecholboranes
2003; Wiley; Volume: 42; Issue: 23 Linguagem: Inglês
10.1002/anie.200351171
ISSN1521-3773
AutoresArnaud‐Pierre Schaffner, Philippe Renaud,
Tópico(s)Chemical Synthesis and Analysis
ResumoAngewandte Chemie International EditionVolume 42, Issue 23 p. 2658-2660 Communication Tin-Free Radical Allylation of B-Alkylcatecholboranes† Arnaud-Pierre Schaffner, Arnaud-Pierre Schaffner University of Berne, Department of Chemisty and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland, Fax: (+41) 31-631-3426Search for more papers by this authorPhilippe Renaud Prof. Dr., Philippe Renaud Prof. Dr. [email protected] University of Berne, Department of Chemisty and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland, Fax: (+41) 31-631-3426Search for more papers by this author Arnaud-Pierre Schaffner, Arnaud-Pierre Schaffner University of Berne, Department of Chemisty and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland, Fax: (+41) 31-631-3426Search for more papers by this authorPhilippe Renaud Prof. Dr., Philippe Renaud Prof. Dr. [email protected] University of Berne, Department of Chemisty and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland, Fax: (+41) 31-631-3426Search for more papers by this author First published: 12 June 2003 https://doi.org/10.1002/anie.200351171Citations: 67 † This work was supported by the Swiss National Science Foundation (grants 21-67106.01 and 7SUPJ062348). We thank Callery Chemical Company (Pittsburgh) and Z&S Handel AG (Kloten) for the gift of catecholborane. 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 Organoboranes, prepared in situ by hydroboration of olefins with catecholborane, are efficiently allylated with allyl sulfones by a radical fragmentation process (see scheme). This hydroallylation of alkenes proved to be general for a wide range of alkenes and allyl sulfones. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z51171_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 1aB. Giese, Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds, Pergamon, Oxford, 1986; 1bW. B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992; 1cJ. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Synthesis, Wiley, Chichester, 1995; 1d Radicals in Organic Synthesis, Vol. 1 and 2 (Ed ), Wiley-VCH, Weinheim, 2001. 2 2aC. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415; 2bH. Yorimitsu, K. Oshima in Radicals in Organic Synthesis, Vol. 1 (Ed ), Wiley-VCH, Weinheim, 2001, p. 11. 3 3aC. Ollivier, P. 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