Gold-catalyzed hydroarylation of alkynes

European Journal of Organic Chemistry

Volumn , Issue 18, 2003, Pages 3485-3496

  Reetz, Manfred T ^a   Sommer, Knut ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkynes; Aromatic substitution; C H Activation; Gold; Homogeneous catalysis

Indexed keywords

ACETYLENE DERIVATIVE; ACETYLENECARBOXYLIC ACID ESTER; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; GOLD; GOLD DERIVATIVE; PALLADIUM; PHENYLACETYLENE; PLATINUM; SILVER DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; ARYLATION; CATALYSIS; COMPLEX FORMATION; ELECTRON TRANSPORT; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0141615958     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300260     Document Type: Article

References (74)

1. [1a] S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature (London, U. K.) 1993, 366, 529-531.
2. [1b] S. Murai, F. Kakiuchi S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Pure Appl. Chem. 1994, 66, 1527-1534.
3. [1c] S. Murai, J. Synth. Org. Chem. Jpn. 1994, 56, 992-1001.
4. [1d] F. Kakiuchi, Y. Yamamoto, N. Chatani, S. Murai, Chem. Lett. 1995, 681-682.
5. [1e] F. Kakiuchi, Y. Tanaka, T. Sato, N. Chatani, S. Murai, Chem. Lett. 1995, 679-680.
6. [1f] F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc., Jpn. 1995, 68, 62-83.
7. [1g] Y.-G. Lim, J.-B. Kang, Y. H. Kim, J. Chem. Soc., Perkin Trans. 1 1996, 2201-2206.
8. [h] C.-H. Jun, C. W. Moon, J.-B. Hong, S.-G. Lim, K.-Y. Chung, Y.-H. Kim, Chem. Eur. J. 2002, 8, 485-492.
9. 2: [2a] Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166-7169.
10. [2b] M. Watanabe, M. Yamamura, I. Moritani, Y. Fujiwara, A. Sonoda, Bull. Chem. Soc., Jpn. 1974, 47, 1035-1036.
11. [2c] Y. Fuchita, K. Hiraki, Y. Kamogawa, M. Suenaga, K. Tohgoh, Y. Fujiwara, Bull. Chem. Soc., Jpn. 1989, 62, 1081-1085.
12. II: [3a] K. Mikami, M. Hatano, M. Terada, Chem. Lett. 1999, 55-56.
13. [3b] C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097-2100.
14. [3c] M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586-1587.
15. III: [3d] T. Matsumoto, D. J. Taube, R. A. Periana, H. Taube, H. Yoshida, J. Am. Chem. Soc. 2000, 122, 7414-7415.
16. [3e] T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Mol. Catal A.: Chem. 2002, 180, 1-18.
17. III: [3f] V. V. Grushin, W. J. Marshall, D. L. Thorn, Adv. Synth. Catal. 2001, 343, 161-165.
18. For reviews on C-H activation see: [4a] A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932.
19. [4b] G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1698-1712.
20. [4b] G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1698-1712.
21. [4c] C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639.
22. [4d] V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1770.
23. A. Fürstner, D. Voigtländer, W. Schrader, D. Giebel, M. T. Reetz, Org. Lett. 2001, 3, 417-420; and references cited therein.
24. [6a] M. S. Kharasch, H. S. Isbell, J. Am. Chem. Soc. 1931, 53, 3053-3059.
25. [6b] K. S. Liddle, C. Parkin, J. Chem. Soc., Chem. Commun. 1972, 26.
26. [6c] P. W. J. de Graaf, J. Boersma, G. J. M. van der Kerk, J. Organomet. Chem. 1976, 105, 399-406.
27. [6d] Y. Fuchita, Y. Utsunomiya, M. Yasutake, J. Chem. Soc., Dalton Trans. 2001, 2330-2334.
28. K. Sommer, projected dissertation, 2003.
29. [8a] C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252-7263.
30. [8b] C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992-1995.
31. [8c] C. Jia, D. Piao, T. Kitamura, Y. Fujiwara, J. Org. Chem. 2000, 65, 7516-7522.
32. [8d] C. Jia, T. Kitamura, Y. Fujiwara, J. Synth. Org. Chem. Jpn. 2001, 59, 1052-1060.
33. T. Tsuchimoto, T. Maeda, E. Shirakawa, Y. Kawakami, Chem. Commun. (Cambridge, U. K.) 2000, 1573-1574.
34. G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, G. Gnappi, Tetrahedron Lett. 1995, 36, 9177-9180.
35. Gold(I)-catalyzed Aldol reactions: [11a] Y. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405-6406.
36. [11b] T. Hayashi, M. Sawamura, Y. Ito, Tetrahedron 1992, 48, 1999-2012.
37. [11c] A. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649-1664.
38. [11d] P. F. Hughes, S. H. Smith, J. T. Olson, J. Org. Chem. 1994, 59, 5799-5802.
39. Gold(III)-catalyzed C-C, C-O and C-N bond coupling reactions: [12a] A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
40. Gold(III)-catalyzed C-C, C-O and C-N bond coupling reactions: [12a] A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
41. [12b] A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27.
42. [12c] A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771.
43. [12d] A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554.
44. [12e] A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
45. [12f] N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651.
46. [12g] S. Kobayashi, K. Kakumoto, M. Sugiura, Org. Lett. 2002, 4, 1319-1322.
47. [12h] A. Arcadi, G. Bianchi, S. Di Giuseppe, F. Marinelli, Green Chem. 2003, 5, 64-67.
48. Recent Reviews on gold-catalysis: [13a] G. Dyker, Angew. Chem. 2000, 112, 4407-4409; Angew. Chem. Int. Ed. 2000, 39, 4237-4239.
49. Recent Reviews on gold-catalysis: [13a] G. Dyker, Angew. Chem. 2000, 112, 4407-4409; Angew. Chem. Int. Ed. 2000, 39, 4237-4239.
50. [13b] G. C. Bond, Catal. Today 2002, 72, 5-9.
51. [14a] A. Fürstner, V. Mamane, J. Org. Chem. 2002, 67, 6264-6267. See also:
52. [14b] S. J. Pastine; S. W. Youn; D. Sames, Org. Lett. 2003, 5, 1055-1058.
53. H. J. Cristau, M. Taillefer, Tetrahedron 1998, 54, 1507-1522.
54. A. W. McCulloch, A. G. McInnes, Can. J. Chem. 1971, 49, 3152-3157.
55. Gold(III)-catalyzed addition of oxygen nucleophiles to alkynes: [17a] R. O. C. Norman, W. J. E. Parr, C. B. Thomas, J. Chem. Soc., Perkin Trans. 1 1976, 1983-1987.
56. [17b] Y. Fukuda, K. Utimoto, J. Org. Chem. 1991, 56, 3729-3731.
57. [17c] Y. Fukuda, K. Utimoto, Bull. Chem. Soc., Jpn. 1991, 64, 2013-2015.
58. [17d] Y. Fukuda, K. Utimoto, Synthesis 1991, 975-978.
59. [17e] F. Gasparrini, M. Giovannoli, D. Misiti, G. Natile, G. Palmieri, L. Maresca, J. Am. Chem. Soc. 1993, 115, 4401-4402.
60. Nitrogen nucleophiles: [17f] M. Deetlefs, H. G. Raubenheimer, M. W. Esterhuysen, Catal. Today 2002, 72, 29-41.
61. [17g] A. Arcadi, S. D. Giuseppe, F. Marinelli, E. Rossi, Adv. Synth. Catal. 2001, 343, 443-446.
62. Gold(I)-catalyzed addition of oxygen nucleophiles to alkynes: [18a] J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478; Angew. Chem. Int. Ed. 1998, 37, 1415-1418.
63. Gold(I)-catalyzed addition of oxygen nucleophiles to alkynes: [18a] J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478; Angew. Chem. Int. Ed. 1998, 37, 1415-1418.
64. [18b] J. H. Teles, M. Schulz, BASF AG, WO-A 97/21648, 1997 [Chem. Abstr. 1997, 127, 121499u].
65. [18c] E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 2002, 114, 4745-4747; Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
66. [18c] E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. 2002, 114, 4745-4747; Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
67. P. C. Leung, K. C. Lee, F. Aubke, Can. J. Chem. 1979, 57, 326-329.
68. It turned out that in the Friedel-Crafts acylation of anisole the isolated compound 44 gave significant lower conversions than the unfiltered reaction mixture.[7]
69. In some spectra a sharp signal at δ = 44.4 ppm was observed, which we believe to belong to a decomposition product containing a P=O group.
70. III salts also catalyze these reactions.
71. J. B. Lambert, E. G. Larson, R. J. Bosch, M. L. E. TeVrucht, J. Am. Chem. Soc. 1985, 107, 5443-5447.
72. Synthesis of 1-(p-methoxyphenyl)-2-(trimethylsilyl)acetylene: C.-M. Che, W.-Y. Yu, P.-M. Chan, W.-C. Cheng, S.-M. Peng, K.-C. Lau, W.-K. Li, J. Am. Chem. Soc. 2000, 122, 11380-11392. The TMS compound was hydrolyzed with KOH in aqueous MeOH (2 h, room temp.) to give p-methoxyphenyl-acetylene.
73. P. S. Bailey, H. H. Hwang, C.-Y. Chiang, J. Org. Chem. 1985, 50, 231-234.
74. H. G. O. Becker, Organikum, Johann Ambrosius Barth Verlag, Heidelberg-Leibzig, Germany, 20th edition, 1996, p. 442.