Synthesis of 2-phenylnaphthalenes through gold-catalyzed dimerization via a highly selective carbon nucleophile pathway

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4514-4521

  Wang, Sinan ^a   Zhang, Lei ^a   Ding, Xiao ^a   Zhou, Yu ^a   Wang, Jinfang ^a   Jiang, Hualiang ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2--PHENYLNAPHTHALENE; CARBON NUCLEOPHILES; FACILE SYNTHESIS; NUCLEOPHILIC CENTERS; SELECTIVE FORMATION;

AMIDES; DIMERIZATION; NAPHTHALENE; SCAFFOLDS;

SMECTIC LIQUID CRYSTALS;

2 PHENYLNAPHTHALENE; ACETIC ACID; AMIDE; CARBON; GOLD; NAPHTHALENE DERIVATIVE; NITROGEN; NUCLEOPHILE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIMERIZATION; NUCLEOPHILICITY; SYNTHESIS;

AMIDES; CARBON; CATALYSIS; DIMERIZATION; GOLD; NAPHTHALENES; NITROGEN; OXYGEN; SUBSTRATE SPECIFICITY;

EID: 79957834618     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200352j     Document Type: Article

References (54)

1. For recent reviews on gold-catalyzed reactions, see: Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896
2. Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395
3. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
4. Arcadi, A. Chem. Rev. 2008, 108, 3266
5. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
6. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
7. Lipshutz, B. H.; Yamamoto, Y. Chem. Rev. 2008, 108, 2793
8. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395
9. Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391
10. Antoniotti, S.; Genin, E.; Michelet, V.; Genet, J. P. J. Am. Chem. Soc. 2005, 127, 9976
11. Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027
12. Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genet, J. P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112
13. Dai, L. Z.; Qi, M. J.; Shi, Y. L.; Liu, X. G.; Shi, M. Org. Lett. 2007, 9, 3191
14. Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259
15. Hashmi, A. S. K.; Schuster, A. M.; Rominger, F. Angew. Chem, Int. Ed. 2009, 48, 8247
16. Weyrauch, J. P.; Hashmi, A. S. K.; Schuster, A.; Hengst, T.; Schetter, S.; Littmann, A.; Rudolph, M.; Hamzic, M.; Visus, J.; Rominger, F.; Frey, W.; Bats, J. W. Chem.-Eur. J. 2010, 16, 956
17. Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500
18. Kang, J. E.; Kim, H. B.; Lee, J. W.; Shin, S. Org. Lett. 2006, 8, 3537
19. Nakamura, I.; Yamagishi, U.; Song, D.; Konta, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 2284
20. Zhang, Z.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2007, 46, 283
21. Hashmi, A. S. K.; Buhrle, M. Aldrichim. Acta 2010, 43, 27
22. Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350
23. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486
24. Amijs, C. H.; Lopez-Carrillo, V.; Echavarren, A. M. Org. Lett. 2007, 9, 4021
25. Yu, Y.; Stephenson, G. A.; Mitchell, D. Tetrahedron Lett. 2006, 47, 3811
26. Zhang, D.; Liu, Z.; Yum, E. K.; Larock, R. C. J. Org. Chem. 2007, 72, 251
27. Marchal, E.; Uriac, P.; Legouin, B.; Toupet, L.; Weghe, P. Tetrahedron 2007, 63, 9979
28. Badry, M. G.; Kariuki, B.; Knight, D. W.; Mohammed, F. K. Tetrahedron Lett. 2009, 50, 1385
29. Zhou, Y.; Feng, E.; Liu, G.; Ye, D.; Li, J.; Jiang, H.; Liu, H. J. Org. Chem. 2009, 74, 7344
30. Feng, E.; Zhou, Y.; Zhang, D.; Zhang, L.; Sun, H.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 3274
31. Zhou, Y.; Zhai, Y.; Ji, X.; Liu, G.; Feng, E.; Ye, D.; Zhao, L.; Jiang, H.; Liu, H. Adv. Synth. Catal. 2010, 352, 373
32. Liu, G.; Zhou, Y.; Ye, D.; Zhang, D.; Ding, X. Adv. Synth. Catal. 2009, 351, 2605
33. Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
34. Zhang, L.; Ye, D.; Zhou, Y.; Liu, G.; Feng, E.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 3671
35. Hashmi, A. S. K.; Schafer, S.; Wolfle, M.; Gil, C. D.; Fischer, P.; Laguna, A.; Blanco, M. C.; Gimeno, M. C. Angew. Chem., Int. Ed. 2007, 46, 6184
36. Hashmi, A. S. K.; Wolfle, M.; Ata, F.; Frey, W.; Rominger, F. Synthesis 2010, 2297
37. CCDC 784559 contains 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.
38. Grise, C. M.; Barriault, L. Org. Lett. 2006, 8, 5905
39. Dudnik, A. S.; Schwier, T.; Gevorgyan, V. Org. Lett. 2008, 10, 1465
40. Park, C.; Lee, P. H. Org. Lett. 2008, 10, 3359
41. Balamurugan, R.; Gudla, V. Org. Lett. 2009, 11, 3116
42. Jiang, M.; Liu, L. P.; Shi, M.; Li, Y. Org. Lett. 2010, 12, 116
43. Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402
44. Toullec, P. Y.; Genin, E.; Leseurre, L.; Genet, J. P.; Michelet, V. Angew. Chem., Int. Ed. 2006, 45, 7427
45. Asao, N.; Aikawa, H.; Tago, S.; Umetsu, K. Org. Lett. 2007, 9, 4299
46. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526
47. Lian, J. J.; Chen, P. C.; Lin, Y. P.; Ting, H. C.; Liu, R. S. J. Am. Chem. Soc. 2006, 128, 11372
48. Tang, J. M.; Liu, T. A.; Liu, R. S. J. Org. Chem. 2008, 73, 8479
49. Zhang, C.; Cui, D. M.; Yao, L. Y.; Wang, B. S.; Hu, Y. Z.; Hayashi, T. J. Org. Chem. 2008, 73, 7811
50. Whiting, D. A. Nat. Prod. Rep. 1985, 2, 191
51. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183
52. Kock, I.; Heber, D.; Weide, M.; Wolschendorf, U.; Clement, B. J. Med. Chem. 2005, 48, 2772
53. Conchon, E.; Anizon, F.; Aboab, B.; Prudhomme, M. J. Med. Chem. 2007, 50, 4669
54. Dong, Y.; Shi, Q.; Pai, H. C.; Peng, C. Y.; Pan, S. L. J. Med. Chem. 2010, 53, 2299