Stille Coupling Involving Bulky Groups Feasible with Gold Cocatalyst†
Juan delPozo
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDesirée Carrasco
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDr. Mónica H. Pérez-Temprano
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDr. Max García-Melchor
Química Física, Edifici C.n. Universitat Autònoma de Barcelona, 08193 Bellaterra, Catalonia (Spain)
Search for more papers by this authorProf. Rosana Álvarez
Dpto. Química Orgánica, Facultad de Química, Universidade de Vigo, Lagoas-Marcosende s/n, 36310 Vigo (Spain)
Search for more papers by this authorCorresponding Author
Prof. Juan A. Casares
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/===Search for more papers by this authorCorresponding Author
Prof. Pablo Espinet
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/===Search for more papers by this authorJuan delPozo
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDesirée Carrasco
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDr. Mónica H. Pérez-Temprano
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Search for more papers by this authorDr. Max García-Melchor
Química Física, Edifici C.n. Universitat Autònoma de Barcelona, 08193 Bellaterra, Catalonia (Spain)
Search for more papers by this authorProf. Rosana Álvarez
Dpto. Química Orgánica, Facultad de Química, Universidade de Vigo, Lagoas-Marcosende s/n, 36310 Vigo (Spain)
Search for more papers by this authorCorresponding Author
Prof. Juan A. Casares
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/===Search for more papers by this authorCorresponding Author
Prof. Pablo Espinet
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/
Química Inorgánica, I. U. CINQUIMA, Facultad de Ciencias, Universidad de Valladolid, 47071 Valladolid (Spain) http://gircatalisishomogenea.blogs.uva.es/===Search for more papers by this authorWe thank the Spanish Ministerio de Ciencia e Innovación (CTQ2010-18901/BQU) and the Junta de Castilla y León (VA281A11-2 and VA373A11-2) for financial support.
Graphical Abstract
Gold-Shuttle: Sperrige Gruppen, die in Stille-Kupplungen mit Stannanen und kostengünstigen Liganden nicht oder nur langsam reagieren, können mittels Dimetall-Katalyse effizient gekuppelt werden. Ein Gold-Cokatalysator befördert die sperrige Gruppe vom Zinn zum Palladium und vermindert dadurch den sterischen Anspruch des Übergangszustands (siehe Schema).
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References
- 1Recent reviews:
- 1aM. H. Pérez-Temprano, J. A. Casares, P. Espinet, Chem. Eur. J. 2012, 18, 1864–1884;
- 1bS. A. Blum, J. J. Hirner, Y. Shi, Acc. Chem. Res. 2011, 44, 603–613.
- 2A. L. Casado, P. Espinet, Organometallics 1998, 17, 3677–3683.
- 3M. Pérez-Temprano, J. A. Casares, A. R. de Lera, R. Álvarez, P. Espinet, Angew. Chem. 2012, 124, 5001–5004;
10.1002/ange.201108043 Google ScholarAngew. Chem. Int. Ed. 2012, 51, 4917–4920.
- 4
- 4aA. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T. D. Ramamurthi, F. Rominger, Angew. Chem. 2009, 121, 8392–8395;
10.1002/ange.200902942 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 8243–8246;
- 4bA. S. K. Hashmi, R. Döpp, C. Lothschütz, M. Rudolph, D. Riedel, F. Rominger, Adv. Synth. Catal. 2010, 352, 1307–1314.
- 5For Sonogashira-like cross-coupling employing palladium/gold instead of palladium/copper systems, see:
- 5aL. A. Jones, S. Sanz, M. Laguna, Catal. Today 2007, 122, 403–406;
- 5bB. Panda, T. K. Sarkar, Tetrahedron Lett. 2010, 51, 301–305.
- 6
- 6aY. Shi, S. M. Peterson, W. W. Haberaecker III, S. A. Blum, J. Am. Chem. Soc. 2008, 130, 2168–2169;
- 6bY. Shi, S. D. Ramgren, S. A. Blum, Organometallics 2009, 28, 1275–1277.
- 7
- 7aY. Shi, K. E. Roth, S. D. Ramgren, S. A. Blum, J. Am. Chem. Soc. 2009, 131, 18022–18023;
- 7bY. Shi, S. D. Ramgren, S. A. Blum, Organometallics 2011, 30, 4811–4813.
- 8A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Ackermann, J. D. B. Becker, M. Rudolph, C. Scholz, F. Rominger, Adv. Synth. Catal. 2012, 354, 133–147.
- 9P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808–4839;
10.1002/ange.200300638 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 4704–4734.
- 10
- 10aA. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978–8985;
- 10bA. L. Casado, P. Espinet, J. Am. Chem. Soc. 2000, 122, 11771–11782.
- 11
- 11aJ. P. Marino, J. F. Long, J. Am. Chem. Soc. 1988, 110, 7916–7917;
- 11bL. S. Liebeskind, R. W. Fengl, J. Org. Chem. 1990, 55, 5359–5364;
- 11cL. S. Liebeskind, J. Wand, Tetrahedron Lett. 1990, 31, 4293–4296;
- 11dL. S. Liebeskind, M. S. Yu, R. H. Yu, J. Wang, K. S. Hagen, J. Am. Chem. Soc. 1993, 115, 9048–9055;
- 11eL. S. Liebeskind, S. W. Riesinger, J. Org. Chem. 1993, 58, 408–413;
- 11fJ. R. Falck, R. K. Bhatt, J. Ye, J. Am. Chem. Soc. 1995, 117, 5973–5982;
- 11gG. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748–2749;
- 11hX. Han, B. M. Stoltz, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 7600–7605;
- 11iR. D. Mazzola, S. Giese, C. L. Benson, F. G. West, J. Org. Chem. 2004, 69, 220–223;
- 11jE. Flöistrup, P. Goede, R. Strömberg, J. Malm, Tetrahedron Lett. 2011, 52, 209–211.
- 12
- 12aA. L. Casado, P. Espinet, Organometallics 2003, 22, 1305–1309;
- 12bV. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905–5911.
- 13N. Meyer, S. Sivanathan, F. Mohr, J. Organomet. Chem. 2011, 696, 1244–1247.
- 14R. V. Bojan, J. M. López-de-Luzuriaga, M. Monge, M. E. Olmos, J. Organomet. Chem. 2010, 695, 2385–2393.
- 15 CRC Handbook of Chemistry and Physics, Internet Version 2005 (Ed.: ), CRC, Boca Raton, FL, 2005; http://www.hbcpnetbase.com.
- 16M. H. Pérez-Temprano, A. Nova, J. A. Casares, P. Espinet, J. Am. Chem. Soc. 2008, 130, 10518–10520.
- 17D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1979, 101, 4992–4998.
- 18For the isomers arising from the oxidative addition and their isomerization, see the following paper and references therein: M. H. Pérez-Temprano, A. M. Gallego, J. A. Casares, P. Espinet, Organometallics 2011, 30, 611–617.
- 19R. Álvarez, M. Pérez, O. Nieto-Faza, A. R. de Lera, Organometallics 2008, 27, 3378–3389.
- 20A. Ariafard, Z. Lin, I. J. S. Fairlamb, Organometallics 2006, 25, 5788–5794. Probably the effect on the tin to gold transmetalation should be similar, as this barrier is related to the electrophilicity of the metal center.
- 21The coupling reaction is continuously producing ISn(nBu)3. Should no other source of Cl be available, this ISn(nBu)3 would react with [AuCl(AsPh3)] to give ClSn(nBu)3 and [AuI(AsPh3)], which is undesired.
- 22
- 22aG. C. Fu, Acc. Chem. Res. 2008, 41, 1555–1564;
- 22bJ. R. Naber, S. L. Buchwald, Adv. Synth. Catal. 2008, 350, 957–961;
- 22cM. Dowlut, D. Mallik, M. G. Organ, Chem. Eur. J. 2010, 16, 4279–4283;
- 22dR. D. Mazzola, S. Giese, C. L. Benson, F. G. West, J. Org. Chem. 2004, 69, 220–223;
- 22eM. García-Melchor, G. Ujaque, F. Maseras, A. Lledós in Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences, Vol. 37 (Eds.: ), Springer, Berlin, 2011, chap. 3, pp. 57–84.
- 23A. Nova, G. Ujaque, F. Maseras, A. Lledós, P. Espinet, J. Am. Chem. Soc. 2006, 128, 14571–14578.
- 24Calculated using Gaussian 09 and the ωB97X-D hybrid functional.
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