A General Strategy for the Perfluoroalkylation of Arenes and Arylbromides by Using Arylboronate Esters and [(phen)CuR F ]
2011; Wiley; Volume: 51; Issue: 2 Linguagem: Inglês
10.1002/anie.201106668
ISSN1521-3773
AutoresNichole D. Litvinas, Patrick S. Fier, John F. Hartwig,
Tópico(s)Catalytic Cross-Coupling Reactions
ResumoAngewandte Chemie International EditionVolume 51, Issue 2 p. 536-539 Communication A General Strategy for the Perfluoroalkylation of Arenes and Arylbromides by Using Arylboronate Esters and [(phen)CuRF]† Dr. Nichole D. Litvinas, Dr. Nichole D. Litvinas Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Search for more papers by this authorPatrick S. Fier, Patrick S. Fier Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Search for more papers by this authorProf. Dr. John F. Hartwig, Corresponding Author Prof. Dr. John F. Hartwig [email protected] Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)Search for more papers by this author Dr. Nichole D. Litvinas, Dr. Nichole D. Litvinas Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Search for more papers by this authorPatrick S. Fier, Patrick S. Fier Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Search for more papers by this authorProf. Dr. John F. Hartwig, Corresponding Author Prof. Dr. John F. Hartwig [email protected] Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA) Department of Chemistry, University of Illinois, Urbana-Champaign, Urbana, IL 61801 (USA)Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA)Search for more papers by this author First published: 14 November 2011 https://doi.org/10.1002/anie.201106668Citations: 233 † We thank the NIH for funding (GM-58108 to J.F.H. and 1F32M093540-01 to N.D.L.). Carl Liskey is acknowledged for helpful discussions. phen=phenanthroline; RF=perfluoroalkylated residue 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 versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuRF]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF3] is now commercially available and has been prepared on 20 g scale. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201106668_sm_miscellaneous_information.pdf1.2 MB miscellaneous_information 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. Mueller, C. Faeh, F. Diederich, Science 2007, 317, 1881–1886; 1bS. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320–330; 1cT. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470–477; 1dM. 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