Silylative coupling of terminal alkynes with iodosilanes: New catalytic activation of sp-hybridized carbon-hydrogen bonds

Organometallics

Volumn 30, Issue 9, 2011, Pages 2539-2545

  Kownacki, Ireneusz ^a   Marciniec, Bogdan ^a   Dudziec, Beata ^a   Kubicki, MacIej ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; CARBON-HYDROGEN BOND; CATALYTIC ACTIVATION; CATALYZED REACTIONS; DIRECT ACTIVATION; EQUIMOLAR REACTIONS; FUNCTIONALIZED; H-BONDS; REACTION SUBSTRATES; SILYLATIVE COUPLING; TERMINAL ALKYNE;

ACETYLENE; HYDROGEN BONDS; IRIDIUM;

SYNTHESIS (CHEMICAL);

EID: 79955590749     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200038r     Document Type: Article

References (114)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1999.
2. Casida, J. E. J. Agric. Food Chem. 1991, 39, 1335
3. Anderson, C. J.; Munday, R. H. J. Org. Chem. 2004, 69, 8971
4. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627
5. Uenishi, J.; Matsui, K. Tetrahedron Lett. 2001, 42, 4353
6. Tykwinski., R. R. Angew. Chem., Int. Ed. 2003, 42, 1566
7. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979
8. Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829
9. Yamamoto, Y. Chem. Rev. 2008, 108, 3199
10. Tour, J. Acc. Chem. Res. 2000, 33, 791
11. Carrolland, R. L.; Gorman, Ch. B. Angew. Chem., Int. Ed. 2002, 41, 4378
12. Nishihara, Y.; Ando, J.; Kato, T.; Mori, A. Macromolecules 2000, 33, 2779
13. Martinand, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350
14. Castanet, A.-S.; Colobert, F.; Schlama, T. Org. Lett. 2000, 2, 3559
15. Blumrnkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857
16. Davidsohn, W. E.; Henry, M. C. Chem. Rev. 1967, 67, 73
17. Colvin, E. Silicon in Organic Synthesis; Butterworths: London, 1981; p 165.
18. Brandsma, L.; Verkruijsse, H. D. Synthesis 1999, 1727
19. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; p 129.
20. Anreev, A. A.; Konshin, V. V.; Komarov, N. V.; Rubin, M.; Brouwer, C.; Gevorgyan, V. Org. Lett. 2004, 6, 421
21. Jiang, H.; Zhu, S. Tetrahedron Lett. 2005, 46, 517
22. Rahaim, R. J., Jr.; Shaw, J. T. J. Org. Chem. 2008, 73, 2912
23. Shimizu, R.; Fuchikami, T. Tetrahedron Lett. 2000, 41, 907
24. Fürstner, A.; Mathes, Ch. Org. Lett. 2001, 3, 221
25. Marciniec, B.; Dudziec, B.; Kownacki, I. Angew. Chem., Int. Ed. 2006, 45, 8180
26. Marciniec, B.; Dudziec, B.; Szubert, K. Polish Patent Application P 380 422, 2006
27. Marciniec, B.; Dudziec, B.; Szubert, K.; Walkowiak, J. WO 2008020774, 2008.
28. Dudziec, B.; Marciniec, B. Organometallics 2008, 27, 5598
29. Marciniec, B. Acc. Chem. Res. 2007, 40, 943
30. Kownacki, I.; Marciniec, B.; Dudziec, B.; Kownacka, A. Polish Patent Application P 393475, 2010.
31. Kownacki, I.; Marciniec, B.; Dudziec, B.; Majchrzak, M.; Kownacka, A. Polish Patent Application P 393476, 2010.
32. Kownacki, I.; Marciniec, B. Polish Patent Application P 394454, 2011.
33. Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422
34. Strauss, F. Liebigs Ann. Chem. 1905, 342, 190
35. Bianchini, C.; Peruzzini, M.; Zanobini, F.; Frediani, P.; Albinati, A. J. Am. Chem. Soc. 1991, 113, 5453
36. Dahlenburg, L.; Frosin, K.-M.; Kerstan, S.; Werner, D. J. Organomet. Chem. 1991, 407, 115
37. Echavarren, A. M.; Lopez, J.; Santos, A.; Montoya, J. J. Organomet. Chem. 1991, 414, 393
38. Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59
39. Bruce, M. I. Chem. Rev. 1991, 91, 197
40. Schafer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315
41. Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604
42. Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rew. 1998, 98, 2599
43. Dyker, G. Angew. Chem. 1999, 38, 1698
44. Li, C. J.; Wei, C. M. Chem. Commun. 2002, 268
45. Wei, C. M.; Li, C. J. Green Chem. 2002, 39
46. Yi, Ch. S.; Yun, S. Y.; Guzei, L. A. J. Am. Chem. Soc. 2005, 127, 5782
47. Singer, H.; Wilkinson, G. J. Chem. Soc. (A) 1968, 849
48. Schmitt, H. J.; Singer, H. J. Organomet. Chem. 1978, 153, 165
49. Schafer, H.; Marcy, R.; Ruping, T.; Singer, H. J. Organomet. Chem. 1982, 240, 17
50. Carlton, L.; Read, G. J. Chem. Soc., Perkin Trans. 1978, 1, 1631
51. Yoshikawa, S.; Kiji, J.; Furukawa, J. Makromol. Chem. 1977, 178, 1007
52. Aresta, M.; DeFazio, M. J. Organomet. Chem. 1980, 186, 109
53. Albano, P.; Aresta, M. J. Organomet. Chem. 1980, 190, 243
54. Kovalev, I. P.; Yevdakov, K. V.; Strelenko, Y. A.; Vinogradov, M. G.; Nikishin, G. I. J. Organomet. Chem. 1990, 386, 139
55. Yamaguchi, M.; Omata, K.; Hirama, M. Tetrahedron Lett. 1994, 35, 5689
56. Nishimura, T.; Guo, X.-X.; Ohnishi, K.; Hayashi, T. Adv. Synth. Catal. 2007, 349, 2669
57. Katagiri, T.; Tsurugi, H.; Funayama, A.; Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 830
58. Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405
59. Matsuyama, N.; Tsurugi, H.; Satoh, T.; Miura, M. Adv. Synth. Catal 2008, 350, 2274
60. Shirakura, M.; Suginome, M. Org. Lett. 2009, 11, 523
61. Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 5060
62. Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1995.
63. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organis Synthesis; Springer: Berlin, 1998; p 198.
64. Sabourin, E. T. J. Mol. Catal. 1984, 26, 363
65. Trost, B. M.; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 1987, 109, 3486
66. Trost, B. M.; Matsubara, S.; Caringi, J. J. J. Am. Chem. Soc. 1989, 111, 8745
67. Trost, B. M.; Li, C.-J. Synthesis 1994, 1267
68. Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255
69. Trost, B. M.; Frontier, A. J. J. Am. Chem. Soc. 2000, 122, 11727
70. Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816
71. Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Ruhter, G. J. Am. Chem. Soc. 1997, 119, 698
72. Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58
73. Ohshita, J.; Furumori, K.; Matsuguchi, A.; Ishikawa, M. J. Org. Chem. 1990, 55, 3277
74. Bruyere, D.; Grigg, R.; Hinsley, J.; Hussain, R. K.; Korn, S.; De La Cierva, C. O.; Sridharan, V.; Wang, J. Tetrahedron Lett. 2003, 44, 8669
75. Rubin, M.; Markov, J.; Chuprakov, S.; Wink, D. J.; Gevorgyan, V. J. Org. Chem. 2003, 68, 6251
76. Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474
77. Tenaglia, A.; Giordano, L.; Buono, G. Org. Lett. 2006, 8, 4315
78. Yin, J.; Chisholm, J. D. Chem. Commun. 2006, 632
79. Tsukada, N.; Ninomiya, S.; Aoyama, Y.; Inoue, Y. Org. Lett. 2007, 9, 2919
80. Ogata, K.; Sugasawa, J.; Atsuumi, Y.; Fukuzawa, S. Org. Lett. 2010, 12, 148
81. Matsuyama, N.; Tsurugi, H.; Satoh, T.; Miura, M. Adv. Synth. Catal 2008, 350, 2274
82. Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa, S.-I. J. Am. Chem. Soc. 2009, 131, 3176
83. Ogata, K.; Sugasawa, J.; Fukuzawa, S.-I. Angew. Chem., Int. Ed. 2009, 48, 6078
84. Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410
85. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632
86. Ju, Y.; Li, C.-J.; Varma, R. S. QSAR Comb. Sci. 2004, 23, 891
87. Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763
88. Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. - Eur. J. 2003, 9, 2797
89. Gommermann, N.; Gehrig, A.; Knochel, P. Synlett 2005, 2796
90. Gommermann, N.; Knochel, P. Synlett 2005, 2799
91. Yasuike, S.; Kofink, C. C.; Kloetzing, R. J.; Gommermann, N.; Tappe., K.; Gavryushin, A.; Knochel, P. Tetrahedron: Asymmetry 2005, 16, 3385
92. Gommermann., N.; Knochel, P. Tetrahedron 2005, 61, 11418
93. Gommermann, N.; Knochel, P. Chem. - Eur. J. 2006, 12, 4380
94. Knoepfel, T. F.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971
95. Aschwanden., P.; Stephenson, C. R.J.; Carreira, E. M. Org. Lett. 2006, 8, 2437
96. Huang, B. S.; Yao, X. Q.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1528
97. Koradin., C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535
98. Wang, M.; Li, P. H.; Wang, L. Eur. J. Org. Chem. 2008, 2255
99. Groossen, L. J.; Rodriguez, N.; Manjolinho, F.; Lange, P. P. Adv. Synth. Catal. 2010, 352, 2913
100. Lo, V. K. Y.; Liu, Y.; Wong, M. K.; Che, C. M. Org. Lett. 2006, 8, 1529
101. de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512
102. Chen, W.-W.; Bi, H.-P.; Li, Ch.-J. Synlett 2010, 3, 475
103. Kohno, K.; Nakagawa, K.; Yahagi, T.; Choi, J.-C.; Yasuda, H.; Sakakura, T. J. Am. Chem. Soc. 2009, 131, 2784
104. Ohmura, T.; Yarozuya, S.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365
105. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319
106. Satoshi, S.; Takashi, K.; Ishii, Y. Angew. Chem., Int. Ed. 2001, 40, 2534
107. Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2005, 347, 872
108. Ogata, K.; Toyota, A. J. Organomet. Chem. 2007, 692, 4139
109. Esteruelas, M. A.; Lahoz, F. J.; Onate, E.; Oro, L. A.; Rodriguez, L. Organometallics 1996, 15, 823
110. Herde, J. L.; Lambert, J. V.; Senoff, C. V. Inorg. Synth. 1974, 15, 18
111. Kownacki, I.; Kubicki, M.; Marciniec, B. Inorg. Chim. Acta 2002, 334, 301
112. Vrieze, K.; Collman, J. P.; Sears, C. P., Jr.; Kubota, M. Inorg. Synth. 1968, 11, 101
113. Kownacki, I.; Marciniec, B.; Macina, A.; Rubinsztajn, S.; Lamb, D. Appl. Catal. A: Gen. 2007, 317, 53
114. Roberto, D.; Cariati, E.; Psaro, R.; Ugo, R. Organometallics 1994, 13, 4227