Triphenylene-Based Tris(N-Heterocyclic Carbene) Ligand: Unexpected Catalytic Benefits†
Sergio Gonell
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Search for more papers by this authorDr. Macarena Poyatos
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Search for more papers by this authorCorresponding Author
Prof. Eduardo Peris
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)Search for more papers by this authorSergio Gonell
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Search for more papers by this authorDr. Macarena Poyatos
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Search for more papers by this authorCorresponding Author
Prof. Eduardo Peris
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)
Dpto. de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, 12071 Castellón (Spain)Search for more papers by this authorWe gratefully acknowlegde financial support from the MEC of Spain (CTQ2011-24055/BQU) and Bancaixa (P1.1B2010-02 and P1.1B2011-22). We would also like to thank the Ramón y Cajal program (M.P.). S.G. thanks the Ministerio de Ciencia e Innovación for a fellowship. The authors are grateful to the Serveis Centrals d’Instrumentació Científica (SCIC) of the Universitat Jaume I for providing us with spectroscopic and X-Ray facilities. We also thank Bob Crabtree for thoughtful discussions.
Graphical Abstract
Triple play: A novel triphenylene-based tris(N-heterocyclic carbene) ligand with D3h symmetry and a highly π-delocalized system has been prepared and coordinated to palladium and gold (see figure). The catalytic activities of the new complexes have been compared with those of related benzimidazolylidene and a triptycene-based tris(N-heterocyclic carbene) complexes in three reactions.
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References
- 1R. H. Crabtree, New J. Chem. 2011, 35, 18–23.
- 2
- 2aM. Poyatos, J. A. Mata, E. Peris, Chem. Rev. 2009, 109, 3677–3707;
- 2bF. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166–3216; Angew. Chem. Int. Ed. 2008, 47, 3122–3172.
- 3
- 3aA. Zanardi, J. A. Mata, E. Peris, Chem. Eur. J. 2010, 16, 13109–13115;
- 3bA. Zanardi, J. A. Mata, E. Peris, Organometallics 2009, 28, 1480–1483;
- 3cA. Zanardi, J. A. Mata, E. Peris, Organometallics 2009, 28, 4335–4339;
- 3dA. Zanardi, J. A. Mata, E. Peris, J. Am. Chem. Soc. 2009, 131, 14531–14537;
- 3eA. Zanardi, R. Corberan, J. A. Mata, E. Peris, Organometallics 2008, 27, 3570–3576;
- 3fE. Mas-Marzá, J. A. Mata, E. Peris, Angew. Chem. 2007, 119, 3803–3805;
10.1002/ange.200700535 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 3729–3731.
- 4
- 4aB. M. Neilson, A. G. Tennyson, C. W. Bielawski, J. Phys. Org. Chem. 2012, 25, 531–543;
- 4bB. C. Norris, C. W. Bielawski, Macromolecules 2010, 43, 3591–3593;
- 4cK. A. Williams, A. J. Boydston, C. W. Bielawski, Chem. Soc. Rev. 2007, 36, 729–744;
- 4dA. B. Powell, C. W. Bielawski, A. H. Cowley, Comments Inorg. Chem. 2010, 31, 75–82;
- 4eO. Schuster, L. Mercs, M. Albrecht, Chimia 2010, 64, 184–187.
- 5
- 5aO. Guerret, S. Sole, H. Gornitzka, M. Teichert, G. Trinquier, G. Bertrand, J. Am. Chem. Soc. 1997, 119, 6668–6669;
- 5bA. Zanardi, J. A. Mata, E. Peris, Chem. Eur. J. 2010, 16, 10502–10506;
- 5cA. J. Boydston, C. W. Bielawski, Dalton Trans. 2006, 4073–4077;
- 5dA. J. Boydston, K. A. Williams, C. W. Bielawski, J. Am. Chem. Soc. 2005, 127, 12496–12497;
- 5eD. M. Khramov, A. J. Boydston, C. W. Bielawski, Angew. Chem. 2006, 118, 6332–6335;
10.1002/ange.200601583 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 6186–6189;
- 5fM. D. Sanderson, J. W. Kamplain, C. W. Bielawski, J. Am. Chem. Soc. 2006, 128, 16514–16515;
- 5gA. G. Tennyson, R. J. Ono, T. W. Hudnall, D. M. Khramov, J. A. V. Er, J. W. Kamplain, V. M. Lynch, J. L. Sessler, C. W. Bielawski, Chem. Eur. J. 2010, 16, 304–315;
- 5hA. G. Tennyson, E. L. Rosen, M. S. Collins, V. M. Lynch, C. W. Bielawski, Inorg. Chem. 2009, 48, 6924–6933;
- 5iA. Prades, M. Poyatos, J. A. Mata, E. Peris, Angew. Chem. 2011, 123, 7808–7811;
10.1002/ange.201101806 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 7666–7669;
- 5jA. Prades, E. Peris, M. Alcarazo, Organometallics 2012, 31, 4623–4626.
- 6K. A. Williams, C. W. Bielawski, Chem. Commun. 2010, 46, 5166–5168.
- 7
- 7aS. Carboni, C. Gennari, L. Pignataro, U. Piarulli, Dalton Trans. 2011, 40, 4355–4373;
- 7bL. G. Ma, P. Hao, Q. H. Zhang, D. M. Du, H. X. Xu, Tetrahedron: Asymmetry 2007, 18, 878–884;
- 7cP. Brandt, P. Roth, P. G. Andersson, J. Org. Chem. 2004, 69, 4885–4890;
- 7dR. W. Quan, Z. Li, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8156–8157;
- 7eG. B. Jones, B. J. Chapman, Synthesis 1995, 475–497;
- 7fH. C. Kolb, P. G. Andersson, K. B. Sharpless, J. Am. Chem. Soc. 1994, 116, 1278–1291;
- 7gL. A. Castonguay, A. K. Rappe, C. J. Casewit, J. Am. Chem. Soc. 1991, 113, 7177–7183.
- 8
- 8aC. M. Crudden, D. P. Allen, Coord. Chem. Rev. 2004, 248, 2247–2273;
- 8bW. A. Herrmann, Angew. Chem. 2002, 114, 1342–1363;
Angew. Chem. Int. Ed. 2002, 41, 1290–1309.
10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y CAS PubMed Web of Science® Google Scholar
- 9T. Yatabe, M. A. Harbison, J. D. Brand, M. Wagner, K. Mullen, P. Samori, J. P. Rabe, J. Mater. Chem. 2000, 10, 1519–1525.
- 10
- 10aY. Shibasaki, Y. Yamamoto, Multimetallic Catalysts in Organic Synthesis, Wiley-VCH, Weinheim, 2004;
10.1002/3527603557 Google Scholar
- 10bE. K. van den Beuken, B. L. Feringa, Tetrahedron 1998, 54, 12985–13011;
- 10cJ. I. van der Vlugt, Eur. J. Inorg. Chem. 2012, 363–375;
- 10dJ. H. H. Ho, S. W. S. Choy, S. A. Macgregor, B. A. Messerle, Organometallics 2011, 30, 5978–5984;
- 10eN. D. Jones, B. R. James, Adv. Synth. Catal. 2002, 344, 1126–1134;
- 10fJ. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302–312.
- 11
- 11aJ. N. H. Reek, S. Arevalo, R. Van Heerbeek, P. C. J. Kamer, P. Van Leeuwen in Advances in Catalysis, Vol. 49 (Eds.: ), 2006, pp. 71–151;
- 11bB. Helms, J. M. J. Frechet, Adv. Synth. Catal. 2006, 348, 1125–1148;
- 11cD. Astruc, C. R. Chim. 2005, 8, 1101–1107.
- 12
- 12aM. J. Pouy, S. A. Delp, J. Uddin, V. M. Ramdeen, N. A. Cochrane, G. C. Fortman, T. B. Gunnoe, T. R. Cundari, M. Sabat, W. H. Myers, ACS Catal. 2012, 2, 2182–2193;
- 12bM. Katari, M. N. Rao, G. Rajaraman, P. Ghosh, Inorg. Chem. 2012, 51, 5593–5604;
- 12cL. Canovese, F. Visentin, C. Levi, C. Santo, Inorg. Chim. Acta 2012, 391, 141–149;
- 12dE. Alvarado, A. C. Badaj, T. G. Larocque, G. G. Lavoie, Chem. Eur. J. 2012, 18, 12112–12121;
- 12eS. Gaillard, J. Bosson, R. S. Ramon, P. Nun, A. M. Z. Slawin, S. P. Nolan, Chem. Eur. J. 2010, 16, 13729–13740.
- 13X. Zeng, G. D. Frey, R. Kinjo, B. Donnadieu, G. Bertrand, J. Am. Chem. Soc. 2009, 131, 8690–8696.
- 14CCDC 930168 (4) and 930169 (6) 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.
