Title: H<sub>2</sub> Activation and Hydride Transfer to Olefins by Al(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>‐Based Frustrated Lewis Pairs
Abstract: Angewandte ChemieVolume 124, Issue 33 p. 8397-8400 Zuschrift H2 Activation and Hydride Transfer to Olefins by Al(C6F5)3-Based Frustrated Lewis Pairs† Gabriel Ménard, Gabriel Ménard Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANSearch for more papers by this authorProf. Dr. Douglas W. Stephan, Corresponding Author Prof. Dr. Douglas W. Stephan [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANDepartment of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANSearch for more papers by this author Gabriel Ménard, Gabriel Ménard Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANSearch for more papers by this authorProf. Dr. Douglas W. Stephan, Corresponding Author Prof. Dr. Douglas W. Stephan [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANDepartment of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 (Canada) http://www.chem.utoronto.ca/staff/DSTEPHANSearch for more papers by this author First published: 09 July 2012 https://doi.org/10.1002/ange.201203362Citations: 48 † D.W.S. gratefully acknowledges the financial support of the NSERC of Canada and the award of a Canada Research Chair. G.M. is grateful for the support of NSERC and Walter C. Sumner Fellowships. 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 Hydridlieferant: Frustrierte Lewis-Paare aus tBu3P und Al(C6F5)3 aktivieren H2 unter Bildung von [tBu3PH][(μ-H)(Al(C6F5)3)2], das mit nichtaktivierten Olefinen zu RAl(C6F5)2 (R=Et oder Cy) und [tBu3PH][Al(C6F5)4] reagiert. Der vorgeschlagene Reaktionsmechanismus umfasst eine Olefinaktivierung durch Aluminium, was durch die Isolierung des Cyclohexen-Komplexes [Al(C6F5)3⋅(C6H10)] gestützt wird. 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_201203362_sm_miscellaneous_information.pdf174.8 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 1J. A. Osborn, F. H. Jardine, J. F. Young, G. Wilkinson, J. Chem. Soc. A 1966, 1711–1732. 10.1039/j19660001711 CASPubMedWeb of Science®Google Scholar 2P. S. Hallman, D. Evans, J. A. Osborn, G. Wilkinson, Chem. Commun. 1967, 305–306. CASWeb of Science®Google Scholar 3 3aR. Noyori, Angew. Chem. 2002, 114, 2108–2123; 10.1002/1521-3757(20020617)114:12<2108::AID-ANGE2108>3.0.CO;2-Z Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2008–2022; 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO;2-4 CASPubMedWeb of Science®Google Scholar 3bW. S. Knowles, Angew. Chem. 2002, 114, 2096–2107; 10.1002/1521-3757(20020617)114:12<2096::AID-ANGE2096>3.0.CO;2-Z Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1998–2007; 10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8 CASWeb of Science®Google Scholar 3cN. B. Johnson, I. C. Lennon, P. H. Moran, J. A. Ramsden, Acc. Chem. Res. 2007, 40, 1291–1299; 10.1021/ar700114k CASPubMedWeb of Science®Google Scholar 3dS. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402–1411; 10.1021/ar700113g CASPubMedWeb of Science®Google Scholar 3eC. S. Shultz, S. W. Krska, Acc. Chem. Res. 2007, 40, 1320–1326. 10.1021/ar700141v CASPubMedWeb of Science®Google Scholar 4C. L. Lund, M. J. Sgro, R. Cariou, D. W. Stephan, Organometallics 2012, 31, 802–805. 10.1021/om300014r CASWeb of Science®Google Scholar 5S. C. Bart, E. Lobkovsky, P. J. Chirik, J. Am. Chem. Soc. 2004, 126, 13794–13807. 10.1021/ja046753t CASPubMedWeb of Science®Google Scholar 6S. Monfette, Z. R. Turner, S. P. Semproni, P. J. Chirik, J. Am. Chem. Soc. 2012, 134, 4561–4564. 10.1021/ja300503k CASPubMedWeb of Science®Google Scholar 7J. Wristers, J. Am. Chem. Soc. 1975, 97, 4312–4316. 10.1021/ja00848a029 CASWeb of Science®Google Scholar 8G. 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 9 9aY. Peng, B. D. Ellis, X. Wang, P. P. Power, J. Am. Chem. Soc. 2008, 130, 12268–12269; 10.1021/ja805358u CASPubMedWeb of Science®Google Scholar 9bG. H. Spikes, J. C. Fettinger, P. P. Power, J. Am. Chem. Soc. 2005, 127, 12232–12233. 10.1021/ja053247a CASPubMedWeb of Science®Google Scholar 10J. Spielmann, F. Buch, S. Harder, Angew. Chem. 2008, 120, 9576–9580; 10.1002/ange.200804657 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 9434–9438. 10.1002/anie.200804657 CASPubMedWeb of Science®Google Scholar 11P. Jochmann, J. P. Davin, T. P. Spaniol, L. Maron, J. Okuda, Angew. Chem. 2012, 124, 4528–4531; 10.1002/ange.201200690 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 4452–4455. 10.1002/anie.201200690 CASPubMedWeb of Science®Google Scholar 12D. W. Stephan, G. Erker, Angew. Chem. 2010, 122, 50–81; 10.1002/ange.200903708 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 46–76. 10.1002/anie.200903708 CASPubMedWeb of Science®Google Scholar 13 13aG. C. Welch, D. W. Stephan, J. Am. Chem. Soc. 2007, 129, 1880–1881; 10.1021/ja067961j CASPubMedWeb of Science®Google Scholar 13bG. 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 13cM. Ullrich, A. J. Lough, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 52–53. 10.1021/ja808506t CASPubMedWeb of Science®Google Scholar 14 14aP. A. Chase, T. Jurca, D. W. Stephan, Chem. Commun. 2008, 1701–1703; 10.1039/b718598g CASPubMedWeb of Science®Google Scholar 14bP. A. Chase, G. C. Welch, T. Jurca, D. W. Stephan, Angew. Chem. 2007, 119, 8196–8199; 10.1002/ange.200702908 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 8050–8053; 10.1002/anie.200702908 CASPubMedWeb of Science®Google Scholar 14cP. Spies, S. Schwendemann, S. Lange, G. Kehr, R. Frohlich, 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 15H. D. Wang, R. Frohlich, G. Kehr, G. Erker, Chem. Commun. 2008, 5966–5968. 10.1039/b813286k CASPubMedWeb of Science®Google Scholar 16T. Mahdi, Z. M. Heiden, S. Grimme, D. W. Stephan, J. Am. Chem. Soc. 2012, 134, 4088–4091. 10.1021/ja300228a CASPubMedWeb of Science®Google Scholar 17 17aG. Ménard, D. W. Stephan, J. Am. Chem. Soc. 2010, 132, 1796–1797; 10.1021/ja9104792 CASPubMedWeb of Science®Google Scholar 17bG. Ménard, D. W. Stephan, Angew. Chem. 2011, 123, 8546–8549; 10.1002/ange.201103600 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 8396–8399; 10.1002/anie.201103600 CASPubMedWeb of Science®Google Scholar 17cM. A. Dureen, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 8396–8397; 10.1021/ja903650w CASPubMedWeb of Science®Google Scholar 17dG. Ménard, D. W. Stephan, Angew. Chem. 2012, 124, 4485–4488; 10.1002/ange.201200328 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 4409–4412. 10.1002/anie.201200328 CASPubMedWeb of Science®Google Scholar 18 18aY. Zhang, G. M. Miyake, E. Y. X. Chen, Angew. Chem. 2010, 122, 10356–10360; 10.1002/ange.201005534 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 10158–10162; 10.1002/anie.201005534 CASPubMedWeb of Science®Google Scholar 18bJ. Boudreau, M.-A. Courtemanche, F.-G. Fontaine, Chem. Commun. 2011, 47, 11131–11133; 10.1039/c1cc14641f CASPubMedWeb of Science®Google Scholar 18cC. Appelt, H. Westenberg, F. Bertini, A. W. Ehlers, J. C. Slootweg, K. Lammertsma, W. Uhl, Angew. Chem. 2011, 123, 4011–4014; 10.1002/ange.201006901 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 3925–3928. 10.1002/anie.201006901 CASPubMedWeb of Science®Google Scholar 19CCDC 889612–889615 (1 a, 4, 6, and 8) 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 20E. Y. X. Chen, K. A. Abboud, Organometallics 2000, 19, 5541–5543. 10.1021/om000866d CASWeb of Science®Google Scholar 21S. M. Baldwin, J. E. Bercaw, L. M. Henling, M. W. Day, H. H. Brintzinger, J. Am. Chem. Soc. 2011, 133, 1805–1813. 10.1021/ja1050428 CASPubMedWeb of Science®Google Scholar 22Z. Yu, J. M. Wittbrodt, A. Xia, M. J. Heeg, H. B. Schlegel, C. H. Winter, Organometallics 2001, 20, 4301–4303. 10.1021/om010531b CASWeb of Science®Google Scholar 23W. Uhl, A. Vogelpohl, Z. Naturforsch. B 2010, 65, 687–694. 10.1515/znb-2010-0604 CASWeb of Science®Google Scholar 24J. Klosin, G. R. Roof, E. Y. X. Chen, K. A. Abboud, Organometallics 2000, 19, 4684–4686. 10.1021/om000573k CASWeb of Science®Google Scholar 25T. W. Dolzine, J. P. Oliver, J. Am. Chem. Soc. 1974, 96, 1737–1740. 10.1021/ja00813a015 CASWeb of Science®Google Scholar 26X. Zhao, D. W. Stephan, J. Am. Chem. Soc. 2011, 133, 12448–12450. 10.1021/ja205598k CASPubMedWeb of Science®Google Scholar 27H. Schnöckel, M. Leimkühler, R. Lotz, R. Mattes, Angew. Chem. 1986, 98, 929–930; 10.1002/ange.19860981027 Google ScholarAngew. Chem. Int. Ed. Engl. 1986, 25, 921–922. 10.1002/anie.198609211 Web of Science®Google Scholar 28Y. Hu, L. O. Gustafson, H. Zhu, E. Y. X. Chen, J. Polym. Sci. Part A 2011, 49, 2008–2017. 10.1002/pola.24628 CASWeb of Science®Google Scholar 29 29aE. C. Ashby, J. J. Lin, J. Org. Chem. 1978, 43, 2567–2572; 10.1021/jo00407a004 CASWeb of Science®Google Scholar 29bF. Sato, S. Sato, H. Kodama, M. Sato, J. Organomet. Chem. 1977, 142, 71–79; 10.1016/S0022-328X(00)91817-5 CASWeb of Science®Google Scholar 29cP. W. Chum, S. E. Wilson, Tetrahedron Lett. 1976, 17, 15–16. 10.1016/S0040-4039(00)71310-4 Google Scholar 30X. Zhao, D. W. Stephan, Chem. Sci. 2012, 3, 2123–2132 10.1039/c2sc20262j CASWeb of Science®Google Scholar 31M.-C. Chen, J. A. S. Roberts, T. J. Marks, Organometallics 2004, 23, 932–935. 10.1021/om0341698 CASWeb of Science®Google Scholar Citing Literature Volume124, Issue33August 13, 2012Pages 8397-8400 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Publication Year: 2012
Publication Date: 2012-07-09
Language: en
Type: article
Indexed In: ['crossref']
Access and Citation
Cited By Count: 59
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot