Gold-Catalysis: Reactions of Organogold Compounds with Electrophiles

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doi:10.1071/CH10342

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Gold-Catalysis: Reactions of Organogold Compounds with Electrophiles

A. Stephen K. Hashmi ^A ^C, Tanuja Dondeti Ramamurthi ^A, Matthew H. Todd ^B, Althea S.-K. Tsang ^A ^B and Katharina Graf ^A

^A Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
^B School of Chemistry, University of Sydney, NSW 2006, Australia.
^C Corresponding author. Email: hashmi@hashmi.de

Australian Journal of Chemistry 63(12) 1619-1626 http://dx.doi.org/10.1071/CH10342
Submitted: 15 September 2010 Accepted: 18 October 2010 Published: 6 December 2010





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Abstract

Different arylgold(i), one alkynylgold(i), and one vinylgold(i) triphenylphosphane complexes were subjected to electrophilic halogenation reagents. With N-chlorosuccinimid, N-bromosuccinimid, and N-iodosuccinimid as well as the Barluenga reagent, selectively halogenated compounds were obtained. Trifluoroacetic acid, as a source of protons, leads to a clean protodeauration. With N-fluorobenzenesulfonimide or Selectfluor, exclusively a homocoupling was observed. For the precursor of the vinylgold(i) complex, a similar oxidative coupling could be induced by gold(iii) chloride. Reactions with silicon or tin electrophiles failed.

References

[1] (a) G. Dyker, Angew. Chem. 2000, 112, 4407.
| CrossRef |

(b) G. Dyker, Angew. Chem. Int. Ed. 2000, 39, 4237.
| CrossRef |

(d) A. S. K. Hashmi, Gold Bull. 2004, 37, 51.

(e) N. Krause, A. Hoffmann-Röder, Org. Biomol. Chem. 2005, 3, 387.
| CrossRef |

(f) A. S. K. Hashmi, Angew. Chem. 2005, 117, 7150.
| CrossRef |

(g) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2005, 44, 6990.
| CrossRef |

(h) A. S. K. Hashmi, G. Hutchings, Angew. Chem. 2006, 118, 8064.
| CrossRef |

(i) A. S. K. Hashmi, G. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896.
| CrossRef |

(j) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180.
| CrossRef |

(k) A. Arcadi, Chem. Rev. 2008, 108, 3266.
| CrossRef |

(l) E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326.
| CrossRef |

(m) Z. G. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239.
| CrossRef |

(n) A. S. K. Hashmi, Aldrichimica Acta 2010, 43, 27.

[2] A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766.
| CrossRef | PubMed |

[3] (a) A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360.
| CrossRef |

(b) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2010, 49, 5232.
| CrossRef |

[4] (a) For such examples, see: A. S. K. Hashmi, S. Pankajakshan, M. Rudolph, E. Enns, T. Bander, F. Rominger, W. Frey, Adv. Synth. Catal. 2009, 351, 2855. 10.1002/ADSC.200900614
(b) A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. Hamzic, Angew. Chem. 2009, 121, 5962.
| CrossRef |

(c) A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. Hamzic, Angew. Chem. Int. Ed. 2009, 48, 5848.
| CrossRef |

(d) A. S. K. Hashmi, S. Schäfer, M. Wölfle, C. Diez Gil, P. Fischer, A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. 2007, 119, 6297.
| CrossRef |

(e) A. S. K. Hashmi, S. Schäfer, M. Wölfle, C. Diez Gil, P. Fischer, A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. Int. Ed. 2007, 46, 6184.
| CrossRef |

(f) A. S. K. Hashmi, M. Rudolph, H.-U. Siehl, M. Tanaka, J. W. Bats, W. Frey, Chem. Eur. J. 2008, 14, 3703.
| CrossRef |

[5] (a) C. M. Krauter, A. S. K. Hashmi, M. Pernpointner, ChemCatChem 2010, 2, 1226.
| CrossRef |

(b) A. S. K. Hashmi, Catal. Today 2007, 122, 211.
| CrossRef |

[6] (a) J. P. Weyrauch, A. S. K. Hashmi, A. Schuster, T. Hengst, S. Schetter, A. Littmann, M. Rudolph, M. Hamzic, J. Visus, F. Rominger, W. Frey, J. W. Bats, Chem. Eur. J. 2010, 16, 956.
| CrossRef |

(b) S. F. Kirsch, J. T. Binder, B. Crone, A. Duschek, T. T. Haug, C. Liébert, H. Menz, Angew. Chem. Int. Ed. 2007, 46, 2310.
| CrossRef |

(d) B. Crone, S. F. Kirsch, J. Org. Chem. 2007, 72, 5435.
| CrossRef |

(e) A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515.
| CrossRef |

(f) A. Buzas, F. Gagosz, Synlett 2006, , 2727.
| CrossRef |

(g) A. Buzas, F. Istrate, F. Gagosz, Org. Lett. 2006, 8, 1958.
| CrossRef |

(h) Z. Shi, C. He, J. Am. Chem. Soc. 2004, 126, 3596.
| CrossRef |

(i) S. K. Bhargava, F. Mohr, M. A. Bennett, L. L. Welling, A. C. Willis, Organometallics 2000, 19, 5628.
| CrossRef |

[7] (a) A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T. D. Ramamurthi, F. Rominger, Angew. Chem. 2009, 121, 8392.
| CrossRef |

(b) A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T. D. Ramamurthi, F. Rominger, Angew. Chem. Int. Ed. 2009, 48, 8243.
| CrossRef |

(c) A. S. K. Hashmi, R. Döpp, C. Lothschütz, M. Rudolph, D. Riedel, F. Rominger, Adv. Synth. Catal. 2010, 352, 1307.
| CrossRef |

(d) Y. Shi, S. D. Ramgren, S. A. Blum, Organometallics 2009, 28, 1275.
| CrossRef |

[8] A. S. K. Hashmi, T. D. Ramamurthi, F. Rominger, J. Organomet. Chem. 2009, 694, 592.
| CrossRef |

[9] (a) G. Zhang, Y. Peng, L. Cui, L. Zhang, Angew. Chem. Int. Ed. 2009, 48, 3112.
| CrossRef |

(b) L. Cui, G. Zhang, L. Zhang, Bioorg. Med. Chem. Lett. 2009, 19, 3884.
| CrossRef |

[10] For subsequent reports on C–C bond formation by oxidation, see: (a) M. N. Hopkinson, A. Tessier, A. Salisbury, G. T. Giuffredi, L. E. Combettes, A. D. Gee, V. Gouverneur, Chem. Eur. J. 2010, 16, 4739. 10.1002/CHEM.201000322
(b) M. G. Auzias, M. Neuburger, H. A. Wegner, Synlett 2010, , 2443.
| CrossRef |

(d) G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 1474.
| CrossRef |

      For related results, which might proceed by similar steps:(e) A. Kar, N. Mangu, H. M. Kaiser, M. Beller, M. K. Tse, Chem. Commun. 2008, 386. 10.1039/B714928J
      (f) A. Kar, N. Mangu, H. M. Kaiser, M. K. Tse, J. Organomet. Chem. 2009, 694, 524.
         | CrossRef |

[11] J. Barluenga, M. A. Rodríguez, J. M. González, P. J. Campos, Tetrahedron Lett. 1990, 31, 4207.
| CrossRef |

[12] A. S. K. Hashmi, M. C. Blanco, D. Fischer, J. W. Bats, Eur. J. Org. Chem. 2006, , 1387.
| CrossRef |

[13] (a) M. Pažický, A. Loos, M. J. Ferreira, F. Rominger, C. Jäkel, A. S. K. Hashmi, M. M. Limbach, Organometallics 2010, 29, 4448.
| CrossRef |

(b) Compare to the homogeneous gold-catalyzed oxidative esterification reported recently: A. S. K. Hashmi, C. Lothschuetz, M. Ackermann, R. Doepp, S. Anantharaman, B. Marchetti, H. Bertagnolli, F. Rominger, Chem. Eur. J. 2010, 16, 8012.

[14] WSS: Spectral data were obtained from Wiley Subscription Services, Inc. (US).

[15] H. Wu, J. Hynes, Jr, Org. Lett. 2010, 12, 1192.
| CrossRef | PubMed |

[16] A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem. 2008, 73, 316.
| CrossRef | PubMed |

[17] J. Zilberman, Org. Process Res. Dev. 2003, 7, 303.
| CrossRef |

[18] S. Bhattacharya, A. K. Bauri, S. Chattopadhyay, M. Banerjee, Chem. Phys. Lett. 2005, 401, 323.
| CrossRef |

[19] R. S. P. Hsi, W. T. Stolle, J. Labelled Comp. Radiopharm. 1986, 23, 433.
| CrossRef |

[20] M. D’Auria, G. Mauriello, Synthesis 1995, , 248.
| CrossRef |

[21] D. Florentin, B. P. Roques, M. C. Fournie-Zaluski, Bull. Soc. Chim. Fr. 1976, , 1999.

[22] M. Okutani, Y. Mori, J. Org. Chem. 2009, 74, 442.
| CrossRef | PubMed |

[23] D. J. Nelson, C. D. Blue, H. C. Brown, J. Am. Chem. Soc. 1982, 104, 4913.
| CrossRef |

[24] R. A. Outten, G. D. Daves, J. Org. Chem. 1989, 54, 29.
| CrossRef |

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