Nonmetal‐Mediated Fragmentation of P 4 : Isolation of P 1 and P 2 Bis(carbene) Adducts
2009; Wiley; Volume: 121; Issue: 30 Linguagem: Inglês
10.1002/ange.200902344
ISSN1521-3757
AutoresO. Back, G. Kuchenbeiser, B. Donnadieu, Guy Bertrand,
Tópico(s)Organometallic Complex Synthesis and Catalysis
ResumoAngewandte ChemieVolume 121, Issue 30 p. 5638-5641 Zuschrift Nonmetal-Mediated Fragmentation of P4: Isolation of P1 and P2 Bis(carbene) Adducts† Olivier Back, Olivier Back UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGlenn Kuchenbeiser, Glenn Kuchenbeiser UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorBruno Donnadieu, Bruno Donnadieu UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGuy Bertrand Prof., Guy Bertrand Prof. [email protected] UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this author Olivier Back, Olivier Back UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGlenn Kuchenbeiser, Glenn Kuchenbeiser UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorBruno Donnadieu, Bruno Donnadieu UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this authorGuy Bertrand Prof., Guy Bertrand Prof. [email protected] UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403 (USA), Fax: (+1) 951-827-2725 http://research.chem.ucr.edu/groups/bertrand/guybertrandwebpage/Search for more papers by this author First published: 08 July 2009 https://doi.org/10.1002/ange.200902344Citations: 144 † Financial support from the NSF (CHE 0808825) and Rhodia Inc. are gratefully acknowledged. Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 P4 stückweise: Stabile Singulettcarbene reagieren mit weißem Phosphor bei Raumtemperatur unter Bildung von P4-, P3-, P2- und sogar P1-Fragmenten, die durch die Carbeneinheit stabilisiert werden (siehe Bild). Diese Folge aus Aktivierung und Fragmentierung, die bislang den Einsatz von Übergangsmetallen erforderte, könnte auf umweltverträglicherem Weg zu Phosphorverbindungen führen. 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 ange_200902344_sm_miscellaneous_information.pdf166.2 KB 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 1For recent examples of small molecule activation by nonmetals other than carbenes, see: Google Scholar 1aS. J. Geier, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 3476–3477; 10.1021/ja900572x CASPubMedWeb of Science®Google Scholar 1bM. Ullrich, A. J. Lough, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 52–53; 10.1021/ja808506t CASPubMedWeb of Science®Google Scholar 1cS. N. Riduan, Y. Zhang, J. Y. Ying, Angew. Chem. 2009, 121, 3372–3375; 10.1002/ange.200806058 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 3322–3325; 10.1002/anie.200806058 CASPubMedWeb of Science®Google Scholar 1dA. Jana, C. Schulzke, H. W. Roesky, J. Am. Chem. Soc. 2009, 131, 4600–4601; 10.1021/ja900880z CASPubMedWeb of Science®Google Scholar 1eZ. L. Zhu, X. P. Wang, Y. Peng, H. Lei, J. C. Fettinger, E. Rivard, P. P. Power, Angew. Chem. 2009, 121, 2065–2068; 10.1002/ange.200805982 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 2031–2034; 10.1002/anie.200805982 CASPubMedWeb of Science®Google Scholar 1fY. Peng, M. Brinda, B. D. Ellis, J. C. Fettinger, E. Rivard, P. P. Power, Chem. Commun. 2009, 6042–6044; PubMedWeb of Science®Google Scholar 1gY. Peng, B. D. Ellis, X. P. Wang, J. C. Fettinger, P. P. Power, J. Am. Chem. Soc. 2008, 130, 12268–12269; 10.1021/ja805358u CASPubMedWeb of Science®Google Scholar 1hM. A. Dureen, D. W. Stephan, Chem. Commun. 2008, 4303–4305; 10.1039/b808348g CASPubMedWeb of Science®Google Scholar 1iP. A. Chase, D. W. Stephan, Angew. Chem. 2008, 120, 7543–7547; 10.1002/ange.200802596 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 7433–7437; 10.1002/anie.200802596 CASPubMedWeb of Science®Google Scholar 1jD. Holschumacher, T. Bannenberg, C. G. Hrib, P. G. Jones, M. Tamm, Angew. Chem. 2008, 120, 7538–7542; 10.1002/ange.200802705 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 7428–7432; 10.1002/anie.200802705 CASPubMedWeb of Science®Google Scholar 1kP. Spies, S. Schewendemann, S. Lange, G. Kehr, R. Fröhlich, G. Erker, Angew. Chem. 2008, 120, 7654–7657; 10.1002/ange.200801432 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 7543–7546; 10.1002/anie.200801432 CASPubMedWeb of Science®Google Scholar 1lV. Sumerin, F. Schulz, M. Atsumi, C. Wang, M. Nieger, M. Leskela, T. Repo, P. Pyykko, B. Rieger, J. Am. Chem. Soc. 2008, 130, 14117–14119; 10.1021/ja806627s CASPubMedWeb of Science®Google Scholar 1mV. Sumerin, F. Schulz, M. Nieger, M. T. R. Leskela, B. Rieger, Angew. Chem. 2008, 120, 6090–6092; 10.1002/ange.200800935 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 6001–6003; 10.1002/anie.200800935 CASPubMedWeb of Science®Google Scholar 1nG. C. Welch, R. R. S. Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124–1126. 10.1126/science.1134230 CASPubMedWeb of Science®Google Scholar 2 2aY. Z. Wang, B. Quillian, P. R. Wei, C. S. Wannere, Y. Xie, R. B. King, H. F. Schaefer, P. v. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2007, 129, 12412–12413; 10.1021/ja075932i CASPubMedWeb of Science®Google Scholar 2bY. Z. Wang, B. Quillian, P. R. Wei, Y. Xie, C. S. Wannere, R. B. King, H. F. Schaefer, P. v. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2008, 130, 3298–3299. 10.1021/ja800257j CASPubMedWeb of Science®Google Scholar 3Y. Z. Wang, Y. M. Xie, P. R. Wei, R. B. King, H. F. Schaefer, P. von R. Schleyer, Science 2008, 321, 1069–1071; See also: 10.1126/science.1160768 CASPubMedWeb of Science®Google ScholarC. A. Dyker, G. Bertrand, Science 2008, 321, 1050–1051. 10.1126/science.1162926 CASPubMedWeb of Science®Google Scholar 4 4aL. B. Knight, K. Kerr, P. K. Miller, C. A. Arrington, J. Phys. Chem. 1995, 99, 16842–16848; 10.1021/j100046a009 CASWeb of Science®Google Scholar 4bA. H. Cowley, ACS Symp. Ser. 2006, 917, 2–19; 10.1021/bk-2005-0917.ch001 CASWeb of Science®Google Scholar 4cR. West, ACS Symp. Ser. 2006, 917, 166–178; 10.1021/bk-2005-0917.ch012 CASWeb of Science®Google Scholar 4dP. P. Power, Chem. Rev. 1999, 99, 3463–3503. 10.1021/cr9408989 CASPubMedWeb of Science®Google Scholar 5V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Angew. Chem. 2006, 118, 3568–3571; 10.1002/ange.200600987 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 3488–3491. 10.1002/anie.200600987 CASPubMedWeb of Science®Google Scholar 6G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2007, 316, 439–441. 10.1126/science.1141474 CASPubMedWeb of Science®Google Scholar 7A few examples of NH3 activation by a transition metal have been reported, see: Google Scholar 7aC. M. Fafard, D. Adhikari, B. M. Foxman, D. J. Mindiola, O. V. Ozerov, J. Am. Chem. Soc. 2007, 129, 10318–10319; 10.1021/ja0731571 CASPubMedWeb of Science®Google Scholar 7bT. E. Hanna, E. Loblovski, P. J. Chirik, Eur. J. Inorg. Chem. 2007, 2677–2685; 10.1002/ejic.200601134 CASWeb of Science®Google Scholar 7cY. Nakajima, H. Kameo, H. Suzuki, Angew. Chem. 2006, 118, 964–966; 10.1002/ange.200503222 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 950–952; 10.1002/anie.200503222 CASPubMedWeb of Science®Google Scholar 7dJ. Zhao, A. S. Goldman, J. F. Hartwig, Science 2005, 307, 1080–1082. 10.1126/science.1109389 CASPubMedWeb of Science®Google Scholar 8Examples of metal-catalyzed hydroamination of alkynes with NH3 have recently been reported: V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2008, 120, 5302–5306; 10.1002/ange.200801136 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 5224–5228. 10.1002/anie.200801136 CASPubMedWeb of Science®Google Scholar 9 9aD. E. C. Corbridge, Phosphorus—An Outline of its Chemistry, Biochemistry and Technology, 5th ed., Elsevier, Amsterdam, 1995; Google Scholar 9bJ. Emsley, The 13th Element: The Sordid Tale of Murder, Fire, and Phosphorus, Wiley, New York, 2002. Google Scholar 10For recent reviews, see: Google Scholar 10aJ. S. Figueroa, C. C. Cummins, Dalton Trans. 2006, 2161–2168; 10.1039/b602530g CASPubMedWeb of Science®Google Scholar 10bC. C. Cummins, Angew. Chem. 2006, 118, 876–884; 10.1002/ange.200503327 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 862–870; 10.1002/anie.200503327 CASPubMedWeb of Science®Google Scholar 10cM. Peruzzini, L. Gonsalvi, A. Romerosa, Chem. Soc. Rev. 2005, 34, 1038–1047; 10.1039/b510917e CASPubMedWeb of Science®Google Scholar 10dM. Peruzzini, R. R. Abdreimova, Y. Budnikova, A. Romerosa, O. J. Scherer, H. Sitzmann, J. Organomet. Chem. 2004, 689, 4319–4331; 10.1016/j.jorganchem.2004.05.041 CASWeb of Science®Google Scholar 10eM. Ehses, A. Romerosa, M. Peruzzini, Top. Curr. Chem. 2002, 220, 107–140. 10.1007/3-540-45731-3_5 CASWeb of Science®Google Scholar 11For recent reports, see: Google Scholar 11aP. Barbaro, M. Di Vaira, M. Peruzzini, S. S. Costantini, P. Stoppioni, Inorg. Chem. 2009, 48, 1091–1096; 10.1021/ic801859z CASPubMedWeb of Science®Google Scholar 11bW. W. Seidel, O. T. Summerscales, B. O. Patrick, M. D. Fryzuk, Angew. Chem. 2009, 121, 121–123; 10.1002/ange.200803739 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2009, 48, 115–117; 10.1002/anie.200803739 CASPubMedWeb of Science®Google Scholar 11cP. Barbaro, M. Di Vaira, M. Peruzzini, S. S. Costantini, P. Stoppioni, Angew. Chem. 2008, 120, 4497–4499; 10.1002/ange.200800723 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4425–4427; 10.1002/anie.200800723 CASPubMedWeb of Science®Google Scholar 11dM. Caporali, P. Barbaro, L. Gonsalvi, A. Ienco, D. Yakhvarov, M. Peruzzini, Angew. Chem. 2008, 120, 3826–3828; 10.1002/ange.200800470 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 3766–3768. 10.1002/anie.200800470 CASPubMedWeb of Science®Google Scholar 12Main-group-mediated activation of P4 has also been reported; for recent examples, see: Google Scholar 12aJ. J. Weigand, M. Holthausen, R. Frölich, Angew. Chem. 2009, 121, 301–304; 10.1002/ange.200804903 Web of Science®Google ScholarAngew. Chem. Int. Ed. 2009, 48, 295–298; 10.1002/anie.200804903 CASPubMedWeb of Science®Google Scholar 12bW. T. K. Chan, F. Garcia, A. D. Hopkins, L. C. Martin, M. McPartlin, D. S. Wright, Angew. Chem. 2007, 119, 3144–3146; 10.1002/ange.200604267 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 3084–3086; 10.1002/anie.200604267 CASPubMedWeb of Science®Google Scholar 12cY. Xiong, S. Yao, M. Brym, M. Driess, Angew. Chem. 2007, 119, 4595–4597; 10.1002/ange.200701203 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 4511–4513; 10.1002/anie.200701203 PubMedWeb of Science®Google Scholar 12dA. R. Fox, R. J. Wright, E. Rivard, P. P. Power, Angew. Chem. 2005, 117, 7907–7911; 10.1002/ange.200502865 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 7729–7733; 10.1002/anie.200502865 CASPubMedWeb of Science®Google Scholar 12eH. W. Lerner, M. Bolte, K. Karaghiosoff, M. Wagner, Organometallics 2004, 23, 6073–6076. 10.1021/om049348j CASWeb of Science®Google Scholar 13 13aJ. D. Masuda, W. W. Schoeller, B. Donnadieu, G. Bertrand, Angew. Chem. 2007, 119, 7182–7185; 10.1002/ange.200703055 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 7052–7055; 10.1002/anie.200703055 CASPubMedWeb of Science®Google Scholar 13bJ. D. Masuda, W. W. Schoeller, B. Donnadieu, G. Bertrand, J. Am. Chem. Soc. 2007, 129, 14180–14181. See also: 10.1021/ja077296u CASPubMedWeb of Science®Google ScholarJ. M. Lynam, Angew. Chem. 2008, 120, 843–845; 10.1002/ange.200704305 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 831–833. 10.1002/anie.200704305 CASPubMedWeb of Science®Google Scholar 14 14aB. M. Cossairt, M. C. Diawara, C. C. Cummins, Science 2009, 323, 602–602; 10.1126/science.1168260 CASPubMedWeb of Science®Google Scholar 14bB. M. Cossairt, C. C. Cummins, Angew. Chem. 2008, 120, 8995–8998; 10.1002/ange.200803971 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 8863–8866; 10.1002/anie.200803971 CASPubMedWeb of Science®Google Scholar 14cN. A. Piro, C. C. Cummins, J. Am. Chem. Soc. 2008, 130, 9524–9535; 10.1021/ja802080m CASPubMedWeb of Science®Google Scholar 14dA. R. Fox, C. R. Clough, N. A. Piro, C. C. Cummins, Angew. Chem. 2007, 119, 991–994; 10.1002/ange.200604736 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 973–976; 10.1002/anie.200604736 CASPubMedWeb of Science®Google Scholar 14eN. A. Piro, J. S. Figueroa, J. T. McKellar, C. C. Cummins, Science 2006, 313, 1276–1279. 10.1126/science.1129630 CASPubMedWeb of Science®Google Scholar 15V. Lavallo, J. Mafhouz, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 8670–8671. 10.1021/ja047503f CASPubMedWeb of Science®Google Scholar 16CCDC 730165 (D), 730166 (E), 730167 (F), and 730168 (G) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Google Scholar 17 17aV. Lavallo, Y. Canac, C. Prasang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851–5855; 10.1002/ange.200501841 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 5705–5709; 10.1002/anie.200501841 CASPubMedWeb of Science®Google Scholar 17bR. Jazzar, R. D. Dewhurst, J. B. Bourg, B. Donnadieu, Y. Canac, G. Bertrand, Angew. Chem. 2007, 119, 2957–2960; 10.1002/ange.200605083 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 2899–2902. 10.1002/anie.200605083 CASPubMedWeb of Science®Google Scholar 18V. D. Romanenko, L. S. Kachkovskaya, L. N. Markovskii, Zh. Obshch. Khim. 1985, 55, 2140–2141. CASWeb of Science®Google Scholar 19Y. Z. Wang, Y. M. Xie, P. R. Wei, R. B. King, H. F. Schaefer, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2008, 130, 14970–14971. 10.1021/ja807828t CASPubMedWeb of Science®Google Scholar 20V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2006, 312, 722–724. 10.1126/science.1126675 CASPubMedWeb of Science®Google Scholar 21A. Schmidpeter, S. Lochschmidt, A. Willhalm, Angew. Chem. 1983, 95, 561–562; 10.1002/ange.19830950713 CASGoogle ScholarAngew. Chem. Int. Ed. Engl. 1983, 22, 545–546. 10.1002/anie.198305451 Google Scholar 22B. D. Ellis, C. A. Dyker, A. Decken, C. L. B. Macdonald, Chem. Commun. 2005, 1965–1967. 10.1039/b500692a CASPubMedWeb of Science®Google Scholar Citing Literature Volume121, Issue30July 13, 2009Pages 5638-5641 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. 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