A novel twist on an old theme: β-Halovinylsilanes, a new elimination approach to oligoyne assembly

Comptes Rendus Chimie

Volumn 12, Issue 3-4, 2009, Pages 366-377

  Weller, Michael D ^a   Cox, Liam R ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Alkyne; Conjugated systems; Elimination; Molecular encapsulation; Oligoyne; Vinylhalide; Vinylsilane

Indexed keywords

EID: 60449111435     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2008.09.027     Document Type: Article

References (120)

1. Shi Shun A.L.K., and Tykwinski R.R. Angew. Chem. Int. Ed. 45 (2006) 1034
2. Bunz U.H.F. Chem. Rev. 100 (2000) 1605
3. Stone M.T., Heemstra J.M., and Moore J.S. Acc. Chem. Res. 39 (2006) 11
4. Zheng J., and Swager T.M. In: Weder C. (Ed). Poly(arylene ethynylene)s: From Synthesis to Application. Advances in Polymer Science vol. 177 (2005), Springer, Berlin 151
5. Orita A., and Otera J. Chem. Rev. 106 (2006) 5387
6. Eymery F., Iorga B., and Savignac P. Synthesis (2000) 185
7. Köbrich G. Angew. Chem. Int. Ed. Engl. 4 (1965) 49
8. Larock R.C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations (1999), VCH, New York p. 569
9. Peters S.J., Turk M.R., Kiesewetter M.K., Reiter R.C., and Stevenson C.D. J. Am. Chem. Soc. 125 (2003) 11212
10. Métay E., Hu Q., and Negishi E.-I. Org. Lett. 8 (2006) 5773
11. Chelucci G., Capitta F., Baldino S., and Pinna G.A. Tetrahedron Lett. 48 (2007) 6514
12. For some recent examples:
13. Yokoyama T., Kutsumura N., Ohgiya T., and Nishiyama S. Bull. Chem. Soc. Jpn. 80 (2007) 578
14. Sato R., Hamasaka G., Yamamoto T., Muraoka H., Nakajo S., and Ogawa S. Bull. Chem. Soc. Jpn. 80 (2007) 768
15. Fürstner A., De Souza D., Turet L., Fenster M.D.B., Parra-Rapado L., Wirtz C., Mynott R., and Lehmann C.W. Chem. Eur. J. 13 (2007) 115
16. Li Y., Chen J., and Cao X.P. Synthesis (2006) 320
17. Shukla R., Brody D.M., Lindeman S.V., and Rathore R. J. Org. Chem. 71 (2006) 6124
18. For some recent examples:
19. Mangelinckx S., Rooryck S., Jacobs J., and De Kimpe N. Tetrahedron Lett. 48 (2007) 6535
20. Sato K., Asao N., and Yamamoto Y. J. Org. Chem. 70 (2005) 8977
21. Kozawa Y., and Mori M. J. Org. Chem. 68 (2003) 8068
22. Kouwer P.H.J., Jager W.F., Mijs W.J., and Picken S.J. J. Mater. Chem. 13 (2003) 458
23. Ziegler Jr. C.B., Harris S.M., and Baldwin J.E. J. Org. Chem. 52 (1987) 443
24. Mandai T., Yanagi T., Araki K., Morisaki Y., Kawada M., and Otera J. J. Am. Chem. Soc. 106 (1984) 3670
25. Orita A., Yoshioka N., Struwe P., Braier A., Beckmann A., and Otera J. Chem. Eur. J. 5 (1999) 1355
26. Asano M., Inoue M., Watanabe K., Abe H., and Katoh T. J. Org. Chem. 71 (2006) 6942
27. Katritzky A.R., Abdel-Fattah A.A.A., and Wang M. J. Org. Chem. 67 (2002) 7526
28. Fleming I., and Mwaniki J.M. J. Chem. Soc. Perkin Trans. 1 (1998) 1237
29. Smith III A.B., Barbosa J., Wong W., and Wood J.L. J. Am. Chem. Soc. 118 (1996) 8316
30. Brummond K.M., Gesenberg K.D., Kent J.L., and Kerekes A.D. Tetrahedron Lett. 39 (1998) 8613
31. Schwede W., Cleve A., Ottow E., and Wiechert R. Tetrahedron Lett. 34 (1993) 5257
32. Stang P.J., and Dixit V. Synthesis (1985) 962
33. Fleming I., and Harley-Mason J. J. Chem. Soc. (1963) 4771
34. Corey E.J., and Wollenberg R.H. J. Am. Chem. Soc. 96 (1974) 5581
35. Shibasaki M., Torisawa Y., and Ikegami S. Tetrahedron Lett. 23 (1982) 4607
36. Negishi E.-I., King A.O., Klima W.L., Patterson W., and Silveira Jr. A. J. Org. Chem. 45 (1980) 2526
37. McMurry J.E., and Bosch G.K. J. Org. Chem. 52 (1987) 4885
38. Fleming I., and Ramarao C. Org. Biomol. Chem. 2 (2004) 1504
39. Zard S.Z. Chem. Commun. (2002) 1555
40. Tummatorn J., and Dudley G.B. J. Am. Chem. Soc. 130 (2008) 5050
41. Lythgoe B., and Waterhouse I. Tetrahedron Lett. 29 (1978) 2625
42. Bartlett P.A., Green III F.R., and Rose E.H. J. Am. Chem. Soc. 100 (1978) 4852
43. Bellina F., Colzi F., Mannina L., Rossi R., and Viel S. J. Org. Chem. 68 (2003) 10175
44. Hashmi A.S.K., Grundl M.A., Nass A.R., Naumann F., Bats J.W., and Bolte M. Eur. J. Org. Chem. (2001) 4705
45. Van Wuytswinkel G., Verheyde B., Compernolle F., Toppet S., and Dehaen W. J. Chem. Soc. Perkin Trans. 1 (2000) 1337
46. Yanada R., Negoro N., Yanada K., and Fujita T. Tetrahedron Lett. 37 (1996) 9313
47. Ariza X., Bach J., Berenguer R., Farras J., Fontès M., Garcia J., López M., and Ortiz J. J. Org. Chem. 69 (2004) 5307
48. Sato T., Tsuchiya H., and Otera J. Synlett (1995) 628
49. Reich H.J., and Willis Jr. W.W. J. Am. Chem. Soc. 102 (1980) 5967
50. Fleming I., Goldhill J., and Perry D.A. J. Chem. Soc. Perkin Trans. 1 (1982) 1563
51. Bohlmann F. Angew. Chem. 65 (1953) 385
52. Bohlmann F. Chem. Ber. 86 (1953) 657
53. Bohlmann F., and Viehe H.G. Chem. Ber. 87 (1954) 712
54. Bohlmann F. Angew. Chem. 67 (1955) 389
55. Cook C.L., Jones E.R.H., and Whiting M.C. J. Chem. Soc. (1952) 2883
56. Jones E.R.H., Skattebøl L., and Whiting M.C. J. Chem. Soc. (1958) 1054
57. Jones E.R.H., Lee H.H., and Whiting M.C. J. Chem. Soc. (1960) 3483
58. Akiyama S., and Nakagawa M. Tetrahedron Lett. (1964) 719
59. Okuhara K. J. Org. Chem. 41 (1976) 1487
60. Faul D., and Himbert G. Chem. Ber. 121 (1988) 1367
61. Chan T.-H. Acc. Chem. Res. 10 (1977) 442
62. Bernhard W., and Fleming I. J. Organomet. Chem. 271 (1984) 281
63. Takacs B.E., and Takacs J.M. Tetrahedron Lett. 31 (1990) 2865
64. Miller R.B., and McGarvey G. J. Org. Chem. 43 (1978) 4424
65. Miller R.B., and McGarvey G. J. Org. Chem. 44 (1979) 4623
66. Kobayashi Y., Shimazaki T., Taguchi H., and Sato F. J. Org. Chem. 55 (1990) 5324
67. Kobayashi Y., Yoshida S., Asano M., Takeuchi A., and Acharya H.P. J. Org. Chem. 72 (2007) 1707
68. Asaoka M., Takenouchi K., and Takei H. Chem. Lett. (1988) 1225
69. Fleming I., and Lawrence N.J. J. Chem. Soc. Perkin Trans. 1 (1998) 2679
70. Cunico R.F., and Dexheimer E.M. J. Am. Chem. Soc. 94 (1972) 2868
71. Yamaguchi R., Kawasaki H., Yoshitome T., and Kawanisi M. Chem. Lett. (1982) 1485
72. Cunico R.F. J. Org. Chem. 36 (1971) 929
73. Danhesier R.L., and Carini D.J. J. Org. Chem. 45 (1980) 3925
74. Danhesier R.L., Carini D.J., and Kwasigroch C.A. J. Org. Chem. 51 (1986) 3870
75. Marshall J.A., and Maxson K. J. Org. Chem. 65 (2000) 630
76. Nielsen M.B., and Diederich F. Chem. Rev. 105 (2005) 1837
77. Siemsen P., Livingston R.C., and Diederich F. Angew. Chem. Int. Ed. 39 (2000) 2633
78. Flynn A.B., and Ogilvie W.W. Chem. Rev. 107 (2007) 4698
79. Zweifel G., and Leong W. J. Am. Chem. Soc. 109 (1987) 6409
80. Weller M.D., Kariuki B.M., and Cox L.R. Tetrahedron Lett. 49 (2008) 4596
81. Stracker E.C., and Zweifel G. Tetrahedron Lett. 32 (1991) 3329
82. Beignet J., Jervis P.J., and Cox L.R. J. Org. Chem. 73 (2008) 5462
83. Ramalho R., Jervis P.J., Kariuki B.M., Humphries A.C., and Cox L.R. J. Org. Chem. 73 (2008) 1631
84. Jervis P.J., Cox L.R., and Beilstein J. Org. Chem. 3 (2007) 6
85. Ramalho R., Beignet J., Humphries A.C., and Cox L.R. Synthesis (2005) 3389
86. Beignet J., Tiernan J., Woo C.H., Kariuki B.M., and Cox L.R. J. Org. Chem. 69 (2004) 6341
87. Beignet J., and Cox L.R. Org. Lett. 5 (2003) 4231
88. Moser W.H. Tetrahedron 57 (2001) 2065
89. Simpkins S.M.E., Kariuki B.M., Aricó C.S., and Cox L.R. Org. Lett. 5 (2003) 3971
90. M.D. Weller, L.R. Cox, unpublished results.
91. Ramirez F., Desai N.B., and McKelvie N. J. Am. Chem. Soc. 84 (1962) 1745
92. For a related fluoride-catalysed elimination route to alkynes, see:. Ishihara T., Maekawa T., and Ando T. Tetrahedron Lett. 25 (1984) 1377
93. Simpkins S.M.E., Weller M.D., and Cox L.R. Chem. Commun. (2007) 4035
94. Wang C., Batsanov A.S., West K., and Bryce M.R. Org. Lett. 10 (2008) 3069
95. Chalifoux W.A., Ferguson M.J., and Tykwinski R.R. Eur. J. Org. Chem. (2007) 1001 (and references therein)
96. Frampton M.J., and Anderson H.L. Angew. Chem. Int. Ed. 46 (2007) 1028
97. Stahl J., Mohr W., de Quadras L., Peters T.B., Bohling J.C., Martín-Alvarez J.M., Owen G.R., Hampel F., and Gladysz J.A. J. Am. Chem. Soc. 129 (2007) 8282
98. Sugiyama J., and Tomita I. Eur. J. Org. Chem. (2007) 4651
99. Saito S., Takahashi E., and Nakazono K. Org. Lett. 8 (2006) 5133
100. Berná J., Crowley J.D., Goldup S.M., Hänni K.D., Lee A.-L., and Leigh D.A. Angew. Chem. Int. Ed. 46 (2007) 5709
101. Berná J., Goldup S.M., Lee A.-L., Leigh D.A., Symes M.D., Teobaldi G., and Zerbetto F. Angew. Chem. Int. Ed. 47 (2008) 4392
102. Simpkins S.M.E., Kariuki B.M., and Cox L.R. J. Organomet. Chem. 691 (2006) 5517
103. Clark T.D., and Ghadiri M.R. J. Am. Chem. Soc. 117 (1995) 12364
104. Dietrich-Buchecker C., and Sauvage J.-P. Chem. Commun. (1999) 615
105. Watson M.D., Jäckel F., Severin N., Rabe J.P., and Müllen K. J. Am. Chem. Soc. 126 (2004) 1402
106. Ng K.-Y., Cowley A.R., and Beer P.D. Chem. Commun. (2006) 3676
107. Wakabayashi R., Kubo Y., Kaneko K., Takeuchi M., and Shinkai S. J. Am. Chem. Soc. 128 (2006) 8744
108. de Quadras L., Bauer E.B., Mohr W., Bohling J.C., Peters T.B., Martín-Alvarez J.M., Hampel F., and Gladysz J.A. J. Am. Chem. Soc. 129 (2007) 8296
109. Eastmond R., Johnson T.R., and Walton D.R.M. Tetrahedron 28 (1972) 4601
110. Johnson T.R., and Walton D.R.M. Tetrahedron 28 (1972) 5221
111. Gibtner T., Hampel F., Gisselbrecht J.-P., and Hirsch A. Chem. Eur. J. 8 (2002) 408
112. Klinger C., Vostrowsky O., and Hirsch A. Eur. J. Org. Chem. (2006) 1508
113. Zheng Q., and Gladysz J.A. J. Am. Chem. Soc. 127 (2005) 10508
114. Zheng Q., Bohling J.C., Peters T.B., Frisch A.C., Hampel F., and Gladysz J.A. Chem. Eur. J. 12 (2006) 6486
115. Szafert S., and Gladysz J.A. Chem. Rev. 103 (2003) 4175
116. Szafert S., and Gladysz J.A. Chem. Rev. 106 (2006) PR1
117. Eisler S., and Tykwinski R.R. J. Am. Chem. Soc. 122 (2000) 10736
118. Eisler S., Chahal N., McDonald R., and Tykwinski R.R. Chem. Eur. J. 9 (2003) 2542
119. Luu T., Elliott E., Slepkov A.D., Eisler S., McDonald R., Hegmann F.A., and Tykwinski R.R. Org. Lett. 7 (2005) 51
120. Eisler S., Slepkov A.D., Elliott E., Luu T., McDonald R., Hegmann F.A., and Tykwinski R.R. J. Am. Chem. Soc. 127 (2005) 2666