Deprotonierung eines Borhydrids und Synthese eines Carben- stabilisierten Borylanions†
David A. Ruiz
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorGaël Ung
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorDr. Mohand Melaimi
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorCorresponding Author
Prof. Guy Bertrand
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)Search for more papers by this authorDavid A. Ruiz
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorGaël Ung
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorDr. Mohand Melaimi
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
Search for more papers by this authorCorresponding Author
Prof. Guy Bertrand
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)
UCSD-CNRS Joint Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343 (USA)Search for more papers by this authorDie Autoren danken den NIH (R01 GM 68825) und dem DOE (DE-SC0009376) für die finanzielle Unterstützung sowie Dr. C. Moore für die Hilfestellung bei der Röntgenstrukturanalyse.
Graphical Abstract
Ein saures Hydrid! Dank der Anwesenheit eines cyclischen (Alkyl)(amino)carbens (CAAC) und zweier elektronenziehender Nitrilgruppen gelingt die Deprotonierung eines Borhydrids zu einem Carben-stabilisierten Borylanion. Dieses reagiert am Borzentrum mit Kohlenstoff- und Metall-basierten Elektrophilen. Dipp=2,6-Diisopropylphenyl, KHMDS=Kaliumbis(trimethylsilyl)amid.
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 |
|---|---|
| ange_201303457_sm_miscellaneous_information.pdf15.7 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
- 1Übersichten:
- 1aJ. Cid, H. Gulyás, J. J. Carbo, E. Fernandez, Chem. Soc. Rev. 2012, 41, 3558–3570;
- 1bL. Weber, Eur. J. Inorg. Chem. 2012, 5595–5609;
- 1cH. Gulyas, A. Bonet, C. Pubill-Ulldemolins, C. Sole, J. Cid, E. Fernandez, Pure Appl. Chem. 2012, 84, 2219–2231;
- 1dM. Yamashita, Bull. Chem. Soc. Jpn. 2011, 84, 983–999;
- 1eM. Yamashita, K. Nozaki, J. Synth. Org. Chem. Jpn. 2010, 68, 359–369.
- 2Y. Segawa, M. Yamashita, K. Nozaki, Science 2006, 314, 113–115.
- 3Aktuelle Arbeiten:
- 3aN. Dettenrieder, H. M. Dietrich, C. Schaedle, C. Maichle-Moessmer, K. W. Tornroos, R. Anwander, Angew. Chem. 2012, 124, 4537–4541;
10.1002/ange.201200954 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 4461–4465;
- 3bLit. [1d];
- 3cY. Okuno, M. Yamashita, K. Nozaki, Eur. J. Org. Chem. 2011, 3951–3958;
- 3dM. S. Cheung, T. B. Marder, Z. Lin, Organometallics 2011, 30, 3018–3028;
- 3eY. Okuno, M. Yamashita, K. Nozaki, Angew. Chem. 2011, 123, 950–953; Angew. Chem. Int. Ed. 2011, 50, 920–923;
- 3fT. Terabayashi, T. Kajiwara, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2009, 131, 14162–14163.
- 4
- 4aH. Braunschweig, C. W. Chiu, T. Kupfer, K. Radacki, Inorg. Chem. 2011, 50, 4247–4249;
- 4bH. Braunschweig, C.-W. Chiu, K. Radacki, T. Kupfer, Angew. Chem. 2010, 122, 2085–2088; Angew. Chem. Int. Ed. 2010, 49, 2041–2044.
- 5
- 5aH. Braunschweig, A. Damme, R. D. Dewhurst, T. Kramer, S. Östreicher, K. Radacki, A. Vargas, J. Am. Chem. Soc. 2013, 135, 2313–2320;
- 5bH. Braunschweig, P. Brenner, R. D. Dewhurst, M. Kaupp, R. Müller, S. Östreicher, Angew. Chem. 2009, 121, 9916–9919; Angew. Chem. Int. Ed. 2009, 48, 9735–9738;
- 5cH. Braunschweig, M. Burzler, R. D. Dewhurst, K. Radacki, Angew. Chem. 2008, 120, 5732–5735; Angew. Chem. Int. Ed. 2008, 47, 5650–5653.
- 6J. Monot, A. Solovyev, H. Bonin-Dubarle, E. Derat, D. P. Curran, M. Robert, L. Fensterbank, M. Malacria, E. Lacôte, Angew. Chem. 2010, 122, 9352–9355;
10.1002/ange.201004215 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 9166–9169.
- 7E. Bernhardt, V. Bernhardt-Pitchougina, H. Willner, N. Ignatiev, Angew. Chem. 2011, 123, 12291–12294;
10.1002/ange.201105848 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 12085–12088.
- 8R. Kinjo, B. Donnadieu, M. A. Celik, G. Frenking, G. Bertrand, Science 2011, 333, 610–613.
- 9
- 9aD. P. Curran, A. Solovyev, M. Makhlouf Brahmi, L. Fensterbank, M. Malacria, E. Lacôte, Angew. Chem. 2011, 123, 10476–10500;
10.1002/ange.201102717 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 10294–10317;
- 9bA. Solovyev, Q. Chu, S. J. Geib, L. Fensterbank, M. Malacria, E. Lacôte, D. P. Curran, J. Am. Chem. Soc. 2010, 132, 15072–15080.
- 10
- 10aD. Martin, M. Melaimi, M. Soleilhavoup, G. Bertrand, Organometallics 2011, 30, 5304–5313;
- 10bM. Melaimi, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2010, 122, 8992–9032;
10.1002/ange.201000165 Google ScholarAngew. Chem. Int. Ed. 2010, 49, 8810–8849;
- 10cR. 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;
- 10dV. 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.
- 11
- 11aO. Back, M. Henry-Ellinger, C. D. Martin, D. Martin, G. Bertrand, Angew. Chem. 2013, 125, 3011–3015;
10.1002/ange.201209109 Google ScholarAngew. Chem. Int. Ed. 2013, 52, 2939–2943;
- 11bG. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2007, 316, 439–441;
- 11cV. 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.
- 12G. D. Frey, J. D. Masuda, B. Donnadieu, G. Bertrand, Angew. Chem. 2010, 122, 9634–9637; Angew. Chem. Int. Ed. 2010, 49, 9444–9447.
- 13CCDC 931828 (2) 931829 (3), 931831 (4), 931830 (4′) 931832 (5) und 931833 (6) enthalten die ausführlichen kristallographischen Daten zu dieser Veröffentlichung. Die Daten sind kostenlos beim Cambridge Crystallographic Data Centre über www.ccdc.cam.ac.uk/data_request/cif erhältlich.
- 14
- 14aM. M. Olmstead, P. P. Power, K. J. Weese, J. Am. Chem. Soc. 1987, 109, 2541–2542;
- 14bC. W. Chiu, F. P. Gabbaï, Angew. Chem. 2007, 119, 1753–1755; Angew. Chem. Int. Ed. 2007, 46, 1723–1725;
- 14cC. W. Chiu, F. P. Gabbaï, Angew. Chem. 2007, 119, 7002–7005; Angew. Chem. Int. Ed. 2007, 46, 6878–6881.
- 15Y. Segawa, M. Yamashita, K. Nozaki, Angew. Chem. 2007, 119, 6830–6833;
10.1002/ange.200702369 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 6710–6713.
- 16Andere Bor-Gold-Komplexe:
- 16aLit. [5b];
- 16bS. Bontemps, G. Bouhadir, W. Gu, M. Mercy, C.-H. Chen, B. M. Foxman, L. Maron, O. V. Ozerov, D. Bourissou, Angew. Chem. 2008, 120, 1503–1506;
10.1002/ange.200705024 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1481–1484;
- 16cM. Sircoglou, S. Bontemps, M. Mercy, N. Saffon, M. Takahashi, G. Bouhadir, L. Maron, D. Bourissou, Angew. Chem. 2007, 119, 8737–8740;
10.1002/ange.200703518 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 8583–8586;
- 16dS. Bontemps, G. Bouhadir, K. Miqueu, D. Bourissou, J. Am. Chem. Soc. 2006, 128, 12056–12057.
Citing Literature
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.
