Title: Efficient Aryl–(Hetero)Aryl Coupling by Activation of CCl and CF Bonds Using Nickel Complexes of Air‐Stable Phosphine Oxides
Abstract: Angewandte Chemie International EditionVolume 44, Issue 44 p. 7216-7219 Communication Efficient Aryl–(Hetero)Aryl Coupling by Activation of CCl and CF Bonds Using Nickel Complexes of Air-Stable Phosphine Oxides† Lutz Ackermann Dr., Lutz Ackermann Dr. [email protected] Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorRobert Born, Robert Born Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorJulia H. Spatz, Julia H. Spatz Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorDaniel Meyer, Daniel Meyer Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this author Lutz Ackermann Dr., Lutz Ackermann Dr. [email protected] Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorRobert Born, Robert Born Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorJulia H. Spatz, Julia H. Spatz Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this authorDaniel Meyer, Daniel Meyer Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-218-077-425Search for more papers by this author First published: 08 November 2005 https://doi.org/10.1002/anie.200501860Citations: 223 † This research was supported by Prof. Paul Knochel, the DFG (Emmy Noether-Programm), the Fonds der Chemischen Industrie, and the Ludwig-Maximilians-Universität. 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 couple of couplings: Air-stable diamino- and dioxophosphine oxides are used as preligands in the nickel-catalyzed Kumada cross-coupling reactions of aryl Grignard reagents. A sterically hindered preligand allows for highly efficient cross-coupling of aryl fluorides at ambient temperature (acac=acetylacetonate). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501860_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 1K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374–4376. 2R. J. P. Corriu, J. P. Masse, J. Chem. Soc. Chem. Commun. 1972, 144. 3K. Tamao, J. Organomet. Chem. 2002, 653, 23–26. 4P. Knochel, I. Sapountzis, N. Gommermann, in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. ), Wiley-VCH, Weinheim, 2004, pp. 671–698. 5A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004. 6A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350–4386; Angew. Chem. Int. Ed. 2002, 41, 4176–4211. 7T. G. Richmond, Angew. Chem. 2000, 112, 3378–3380; Angew. Chem. Int. Ed. 2000, 39, 3241–3244. 8T. Braun, R. N. Perutz, Chem. Commun. 2002, 2749–2757. 9T. Takahashi, K. Kanno in Modern Organonickel Chemistry (Ed.: ), Wiley-VCH, Weinheim, 2005, pp. 41–55. 10For an unselective coupling with an alkyl Grignard reagent, see: Y. Kiso, K. Tamao, M. Kumada, J. Organomet. Chem. 1973, 50, C 12–C14. 11For a recent study on thermal and microwave-mediated reactions, see: J. W. Dankwardt, J. Organomet. Chem. 2005, 690, 932–938. 12V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500–3503; Angew. Chem. Int. Ed. 2001, 40, 3387–3389. 13See also: 13aF. Mongin, L. Mojovic, B. Guillamet, F. Trecourt, G. Quéguiner, J. Org. Chem. 2002, 67, 8991–8994; 13bK. Lamm, M. Stollenz, M. Meier, H. Görls, B. Walther, J. Organomet. Chem. 2003, 681, 24–36. 14L. Ackermann, R. Born, Angew. Chem. 2005, 117, 2497–2500; Angew. Chem. Int. Ed. 2005, 44, 2444–2447. 15N. V. Dubrovina, A. Börner, Angew. Chem. 2004, 116, 6007–6010; Angew. Chem. Int. Ed. 2004, 43, 5883–5886. 16For the use of alkyl-substituted phosphine oxides in nickel-catalyzed cross-couplings with aryl chlorides, see: 16aG. Y. Li, Angew. Chem. 2001, 113, 1561–1564; Angew. Chem. Int. Ed. 2001, 40, 1513–1516; 16bG. Y. Li, W. J. Marshall, Organometallics 2002, 21, 590–591. 17For a thorough evaluation of a variety of preligands, see the Supporting Information in: V. P. W. Böhm, T. Weskamp, C. W. K. Gstöttmayr, W. A. Herrmann, Angew. Chem. 2000, 112, 1672–1674; Angew. Chem. Int. Ed. 2000, 39, 1602–1604. 18The corresponding arylphosphonate derived from phosphine oxide 11 could not be obtained by standard synthetic procedures; this underscores the steric demand of preligand 11. A practical protocol for the synthesis of arylphosphonates: L. J. Gooßen, M. K. Dezfuli, Synlett 2005, 445–448, and references therein. 19J. R. Goerlich, A. Fischer, P. G. Jonas, R. Schmutzler, Z. Naturforsch. B 1994, 49, 801–811, and references therein. 20For use in CH bond functionalization reactions with aryl chlorides, see: L. Ackermann, Org. Lett. 2005, 7, 3123–3125. 21For the synthesis of a phosphinous acid nickel complex, starting from [Ni(acac)2] and phosphine oxide 15, see: B. Walther, H. Hartung, M. Maschmeier, U. Baumeister, B. Messbauer, Z. Anorg. Allg. Chem. 1988, 566, 121–130. Citing Literature Volume44, Issue44November 11, 2005Pages 7216-7219 ReferencesRelatedInformation
Publication Year: 2005
Publication Date: 2005-10-17
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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