Selective CF Bond Activation: Substitution of Unactivated Alkyl Fluorides using YbI 3
2013; Wiley; Volume: 52; Issue: 46 Linguagem: Inglês
10.1002/anie.201306104
ISSN1521-3773
AutoresAnnika Träff, Mario Janjetovic, Linda Ta, Göran Hilmersson,
Tópico(s)Synthesis and characterization of novel inorganic/organometallic compounds
ResumoAngewandte Chemie International EditionVolume 52, Issue 46 p. 12073-12076 Communication Selective CF Bond Activation: Substitution of Unactivated Alkyl Fluorides using YbI3† Dr. Annika M. Träff, Dr. Annika M. Träff Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorMario Janjetovic, Mario Janjetovic Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorLinda Ta, Linda Ta Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorProf. Dr. Göran Hilmersson, Corresponding Author Prof. Dr. Göran Hilmersson [email protected] Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this author Dr. Annika M. Träff, Dr. Annika M. Träff Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorMario Janjetovic, Mario Janjetovic Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorLinda Ta, Linda Ta Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this authorProf. Dr. Göran Hilmersson, Corresponding Author Prof. Dr. Göran Hilmersson [email protected] Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg (Sweden)Search for more papers by this author First published: 24 September 2013 https://doi.org/10.1002/anie.201306104Citations: 45 † The authors gratefully acknowledge the Swedish Research Council and the University of Gotheburg for financial support. Prof. Per-Ola Norrby is gratefully acknowledged by his contribution of mechanistic insight. 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 F makes the break: The carbon–fluorine single bond is quite strong, thus making aliphatic CF bond scission unusually challenging. A new methodology utilizing YbI3 leads to the conversion of a CF bond into a CI bond, and is compatible with various functional groups. The reaction is exceptionally selective towards alkyl fluorides and proceeds under mild conditions. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie_201306104_sm_miscellaneous_information.pdf1.8 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 1aS. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320; 1bD. O’Hagan, Chem. Soc. Rev. 2008, 37, 308. 2 2aN. Al-Maharik, D. O’Hagan, Aldrichimica Acta 2011, 44, 65; 2bM. Rueda-Becerril, C. C. Sazepin, J. C. T. Leung, T. Okbinoglu, P. Kennepohl, J.-F. Paquin, G. M. Sammis, J. Am. Chem. Soc. 2012, 134, 4026; 2cF. Yin, Z. Wang, Z. Li, C. Li, J. Am. Chem. Soc. 2012, 134, 10401; 2dM. P. Sibi, Y. Landais, Angew. Chem. 2013, 125, 3654; Angew. Chem. Int. Ed. 2013, 52, 3570. 3H. Amii, K. Uneyama, Chem. Rev. 2009, 109, 2119. 4 4aL. Zhang, W. Zhang, J. Liu, J. Hu, J. Org. Chem. 2009, 74, 2850; 4bG. Blessley, P. Holden, M. Walker, J. M. Brown, V. Gouverneur, Org. Lett. 2012, 14, 2754; 4cE. Benedetto, M. Keita, M. Tredwell, C. Hollingworth, J. M. Brown, V. Gouverneur, Organometallics 2012, 31, 1408; 4dA. Hazari, V. Gouverneur, J. M. Brown, Angew. Chem. 2009, 121, 1322; Angew. Chem. Int. Ed. 2009, 48, 1296; 4eK. Mikami, Y. Tomita, Y. Itoh, Angew. Chem. 2010, 122, 3907; Angew. Chem. Int. Ed. 2010, 49, 3819; 4fT. Iida, R. Hashimoto, K. Aikawa, S. Ito, K. Mikami, Angew. Chem. 2012, 124, 9673; Angew. Chem. Int. Ed. 2012, 51, 9535. 5 5aK. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4873; 5bT. Hatakeyama, S. Ito, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 14192; 5cJ. Terao, S. A. Begum, Y. Shinohara, M. Tomita, Y. Naitoh, N. Kambe, Chem. Commun. 2007, 855; 5dC. Douvris, O. V. Ozerov, Science 2008, 321, 1188; 5eW. Gu, M. R. Haneline, C. Douvris, O. V. Ozerov, J. Am. Chem. Soc. 2009, 131, 11203; 5fJ. Choi, D. Y. Wang, S. Kundu, Y. Choliy, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, Science 2011, 332, 1545; 5gK. Matsubara, T. Ishibashi, Y. Koga, Org. Lett. 2009, 11, 1765; S. A. Begum, J. Terao, N. Kombe, Chem. Lett. 2007, 36, 196. 6 6aG. B. Deacon, C. M. Forsyth, P. C. Junk, J. Wang, Chem. Eur. J. 2009, 15, 3082; 6bM. Klahn, U. Rosenthal, Organometallics 2012, 31, 1235. 7R. Anwander, Lanthanides: Chemistry And Use In Organic Synthesis (Ed.: ), Springer, Berlin, 1999, pp. 1–61. 8M. Janjetovic, A. M. Träff, T. Ankner, J. Wettergren, G. Hilmersson, Chem. Commun. 2013, 49, 1826. 9D. Witt, Synthesis 2008, 2491. 10S.-I. Fukuzawa, Y. Hongo, Tetrahedron Lett. 1998, 39, 3521. 11 J. Collin, N. Giuseppone, P. Van de Weghe, Coord. Chem. Rev. 1998, 178–180, 117. 12M. B. Smith, J. March, March’s Advanced Organic Chemistry: Reactions, Mechanism, and Structure, 6th ed., Wiley, Hoboken, 2007, p. 245. 13IUPAC definition of stereospecific. A. D. McNaught, A. Wilkinson, Compendium of Chemical Terminology, 2nd ed., Blackwell Scientific Publications, Oxford, 1997; XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; Updates compiled by A. Jenkins. 14 14aA. Nova, R. Mas-Ballesté, G. Ujaque, P. González-Duarte, Chem. Commun. 2008, 3130; 14bA. Nova, R. Mas-Ballesté, A. Lledós, Organometallics 2012, 31, 1245. Citing Literature Volume52, Issue46November 11, 2013Pages 12073-12076 ReferencesRelatedInformation
Referência(s)