AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives

Tetrahedron

Volumn 64, Issue 5, 2008, Pages 787-796

  Sato, Kenichiro ^a   Menggenbateer, ^a   Kubota, Toshihiko ^a   Asao, Naoki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Anthracene; Benzannulation; Benzyne; Gold catalyst

Indexed keywords

ALKYNYL GROUP; AMPHOLYTE; ANTHRACENE DERIVATIVE; BENZENE DERIVATIVE; BENZENEDIAZONIUM 2 CARBOXYLATE; BENZYNE; DIAZONIUM COMPOUND; DIOXANE; GOLD CHLORIDE; KETONE DERIVATIVE; PHTHALAZINE DERIVATIVE; TRIPTYCENE DERIVATIVE; TRIPTYCYL KETONE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; BENZANNULATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOADDITION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 37149056734     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.083     Document Type: Article

References (122)

1. For reviews, see:
2. Hoffmann R.W. Dehydrobenzene and Cycloalkynes (1967), Academic, New York, NY
3. Biehl E.R., and Khanapure S.P. Acc. Chem. Res. 22 (1989) 275-281
4. Kessar S.V. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, New York, NY 483-515
5. Buchward S.L., and Broene R.D. In: Able E.W., Stone F.G.A., and Willkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford, UK 771-784
6. Pellissier H., and Santelli M. Tetrahedron 59 (2003) 701-730
7. Wenk H.H., Winkler M., and Sander W. Angew. Chem., Int. Ed. 42 (2003) 502-528
8. For recent examples, see:
9. Schuster I.I., Craciun L., Ho D.M., and Pascal Jr. R.A. Tetrahedron 58 (2002) 8875-8882
10. Duong H.M., Bendikov M., Steiger D., Zhang Q., Sonmez G., Yamada J., and Wudl F. Org. Lett. 5 (2003) 4433-4436
11. Lu J., Ho D.M., Vogelaar N.J., Kraml C.M., and Pascal Jr. R.A. J. Am. Chem. Soc. 126 (2004) 11168-11169
12. Ikadai J., Yoshida H., Ohshita J., and Kunai A. Chem. Lett. 34 (2005) 56-57
13. Hayes M.E., Shinokubo H., and Danheiser R.L. Org. Lett. 7 (2005) 3917-3920
14. Dockendorff C., Sahli S., Olsen M., Milhau L., and Lautens M. J. Am. Chem. Soc. 127 (2005) 15028-15029
15. Shou W.-G., Yang Y.-Y., and Wang Y.-G. J. Org. Chem. 71 (2006) 9241-9243
16. Logullo F.M., Seitz A.H., and Friedman L. Org. Synth. Coll. Vol. V (1973) 54-59
17. Asao N., and Sato K. Org. Lett. 8 (2006) 5361-5363
18. For highlights and reviews on the Au-catalyzed reactions, see:
19. Dyker G. Angew. Chem., Int. Ed. 39 (2000) 4237-4239
20. Hashmi A.S.K. Gold Bull. 36 (2003) 3-9
21. Hashmi A.S.K. Gold Bull. 37 (2004) 51-65
22. Arcadi A., and Di Giuseppe S. Curr. Org. Chem. 8 (2004) 795-812
23. Hoffmann-Röder A., and Krause N. Org. Biomol. Chem. 3 (2005) 387-391
24. Hashmi A.S.K. Angew. Chem., Int. Ed. 44 (2005) 6990-6993
25. Ma S., Yu S., and Gu Z. Angew. Chem., Int. Ed. 45 (2006) 200-203
26. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271-2296
27. Hashmi A.S.K., and Hutchings G.J. Angew. Chem., Int. Ed. 45 (2006) 7896-7936
28. Jiménez-Núñez E., and Echavarren A.M. Chem. Commun. (2007) 333-346
29. Gorin D.J., and Toste F.D. Nature 446 (2007) 395-403
30. Asao N., Takahashi K., Lee S., Kasahara T., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 12650-12651
31. Asao N., Nogami T., Lee S., and Yamamoto Y. J. Am. Chem. Soc. 125 (2003) 10921-10925
32. Asao N., Sato K., Menggenbateer, and Yamamoto Y. J. Org. Chem. 70 (2005) 3682-3685
33. Sato K., Asao N., and Yamamoto Y. J. Org. Chem. 70 (2005) 8977-8981
34. Asao N. Synlett (2006) 1645-1656
35. Other examples of benzannulation with gold catalyst, see:
36. Hashmi A.S.K., Frost T.M., and Bats J.W. J. Am. Chem. Soc. 122 (2000) 11553-11554
37. Hashmi A.S.K., Frost T.M., and Bats J.W. Org. Lett. 3 (2001) 3769-3771
38. Dankwardt J.W. Tetrahedron Lett. 42 (2001) 5809-5812
39. Hashmi A.S.K., Frost T.M., and Bats J.W. Catal. Today 72 (2002) 19-27
40. Mamane V., Hannen P., and Fürstner A. Chem.-Eur. J. 10 (2004) 4556-4575
41. Hashmi A.S.K., Rudolph M., Weyrauch J.P., Wölfle M., Frey W., and Bats J.W. Angew. Chem., Int. Ed. 44 (2005) 2798-2801
42. Dyker G., and Hildebrandt D. J. Org. Chem. 70 (2005) 6093-6096
43. Shibata T., Fujiwara R., and Takano D. Synlett (2005) 2062-2066
44. Shibata T., Ueno Y., and Kanda K. Synlett (2006) 411-414
45. Zhao J., Hughes C.O., and Toste F.D. J. Am. Chem. Soc. 128 (2006) 7436-7437
46. Lian J.-J., Lin C.-C., Chang H.-K., Chen P.-C., and Liu R.-S. J. Am. Chem. Soc. 128 (2006) 9661-9667
47. Hildebrandt D., and Dyker G. J. Org. Chem. 71 (2006) 6728-6733
48. Lian J.-J., and Liu R.-S. Chem. Commun. (2007) 1337-1339
49. Oh C.H., Kim A., Park W., Park D.I., and Kim N. Synlett (2006) 2781-2784
50. Benzo[c]pyrylium salts are known to play a diene part in the Diels-Alder reaction with ethyl vinyl ether, see:. Kuznetsov E., Shcherbakova I.V., and Balaban A.T. Adv. Heterocycl. Chem. 50 (1990) 157-254
51. For a review, see:. Nogradi M. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 14 (2003), Georg Thieme, Stuttgart, Germany pp 201-273
52. Tovar J.D., and Swager T.M. J. Org. Chem. 64 (1999) 6499-6504
53. For examples of reactions with pyrylium intermediates, see:
54. Barluenga J., Vázquez-Villa H., Ballesteros A., and González J.M. J. Am. Chem. Soc. 125 (2003) 9028-9029
55. Barluenga J., Vázquez-Villa H., Ballesteros A., and González J.M. Org. Lett. 5 (2003) 4121-4123
56. Zhu J., Germain A.R., and Porco Jr. J.A. Angew. Chem., Int. Ed. 43 (2004) 1239-1243
57. Kusama H., Funami H., Takaya J., and Iwasawa N. Org. Lett. 6 (2004) 605-608
58. Yue D., Ca N.D., and Larock R.C. Org. Lett. 6 (2004) 1581-1584
59. Sato K., Yudha S.S., Asao N., and Yamamoto Y. Synthesis (2004) 1409-1412
60. Barluenga J., Vázquez-Villa H., Ballesteros A., and González J.M. Adv. Synth. Catal. 347 (2005) 526-530
61. Kusama H., Funami H., Shido M., Hara Y., Takaya J., and Iwasawa N. J. Am. Chem. Soc. 127 (2005) 2709-2716
62. Kim N., Kim Y., Park W., Sung D., Gupta A.K., and Oh C.H. Org. Lett. 7 (2005) 5289-5291
63. Gupta A.K., Rhim C.Y., Oh C.H., Maneb R.S., and Han S.-H. Green Chem. 8 (2006) 25-28
64. Yue D., Cá N.D., and Larock R.C. J. Org. Chem. 71 (2006) 3381-3388
65. Bartlett P.D., Ryan M.J., and Cohen S.G. J. Am. Chem. Soc. 64 (1942) 2649-2653
66. Norvez S., and Barzoukas M. Chem. Phys. Lett. 165 (1990) 41-44
67. Korth O., Wiehe A., Kurreck H., and Röder B. Chem. Phys. 246 (1999) 363-372
68. Beyeler A., and Belser P. Coord. Chem. Rev. 230 (2002) 28-38
69. Perepichka D.F., Bendikov M., Meng H., and Wudl F. J. Am. Chem. Soc. 125 (2003) 10190-10191
70. Satrijo A., and Swager T.M. Macromolecules 38 (2005) 4054-4057
71. Marks V., Nahmany M., Gottlieb H.E., and Biali S.E. J. Org. Chem. 67 (2002) 7898-7901
72. Lu J., Zhang J., Shen X., Ho D.M., and Pascal Jr. R.A. J. Am. Chem. Soc. 124 (2002) 8035-8041
73. Iiba E., Hirai K., Tomioka H., and Yoshioka Y. J. Am. Chem. Soc. 124 (2002) 14308-14309
74. Spyroudis S., and Xanthopoulou N. J. Org. Chem. 67 (2002) 4612-4614
75. Spyroudis S., and Xanthopoulou N. Tetrahedron Lett. 44 (2003) 3767-3770
76. Zhu X.Z., and Chen C.F. J. Org. Chem. 70 (2005) 917-924
77. Perchellet E.M., Magill M.J., Huang X., Brantis C.E., Hua D.H., and Perchellet J.-P. Anti-Cancer Drugs 10 (1999) 749-766
78. Yang W., Perchellet E.M., Tamura M., Hua D.H., and Perchellet J.P. Cancer Lett. 188 (2002) 73-83
79. Hua D.H., Tamura M., Huang X., Stephany H.A., Helfrich B.A., Perchellet E.M., Sperfslage B.J., Perchellet J.-P., Jiang S., Kyle D.E., and Chiang P.K. J. Org. Chem. 67 (2002) 2907-2912
80. Perchellet E.M., Wang Y., Weber R.L., Lou K., Hua D.H., and Perchellet J.-P.H. Anti-Cancer Drugs 15 (2004) 929-946
81. Wang Y., Perchellet E.M., Ward M.M., Lou K., Zhao H., Battina S.K., Wiredu B., Hua D.H., and Perchellet J.-P.H. Int. J. Oncol. 28 (2006) 161-172
82. Marc Veen E., Postma P.M., Jonkman H.T., Spek A.L., and Feringa B.L. Chem. Commun. (1999) 1709-1710
83. Yang J.-S., Liu C.-P., and Lee G.-H. Tetrahedron Lett. 41 (2000) 7911-7915
84. Yang J.-S., Lee C.-C., Yau S.-L., Chang C.-C., Lee C.-C., and Leu J.-M. J. Org. Chem. 65 (2000) 871-877
85. Yang J.-S., Liu C.-P., Lin B.C., Tu C.W., and Lee G.H. J. Org. Chem. 67 (2002) 7343-7354
86. Zhu X.Z., and Chen C.F. J. Am. Chem. Soc. 127 (2005) 13158-13159
87. Zong Q.S., and Chen C.F. Org. Lett. 8 (2006) 211-214
88. Han T., and Chen C.F. Org. Lett. 8 (2006) 1069-1072
89. Zong Q.S., Zhang C., and Chen C.F. Org. Lett. 8 (2006) 1859-1862
90. Peng X.-X., Lu H.-Y., Han T., and Chen C.-F. Org. Lett. 9 (2007) 895-898
91. Han T., Zong Q.S., and Chen C.-F. J. Org. Chem. 72 (2007) 3108-3111
92. Zhang C., and Chen C.-F. J. Org. Chem. 72 (2007) 3880-3888
93. Norvez S. J. Org. Chem. 58 (1993) 2414-2418
94. Yang J.-S., and Swager T.M. J. Am. Chem. Soc. 120 (1998) 5321-5322
95. Yang J.-S., and Swager T.M. J. Am. Chem. Soc. 120 (1998) 11864-11873
96. Yang J.-S., Lin C.-S., and Hwang C.-Y. Org. Lett. 3 (2001) 889-892
97. Long T.M., and Swager T.M. J. Am. Chem. Soc. 124 (2002) 3826-3827
98. Zhu Z., and Swager T.M. J. Am. Chem. Soc. 124 (2002) 9670-9671
99. Long T.M., and Swager T.M. J. Am. Chem. Soc. 125 (2003) 14113-14119
100. Iwamura H., and Mislow K. Acc. Chem. Res. 21 (1988) 175-182
101. Kelly T.R., Bowyer M.C., Bhaskar K.V., Bebbington D., Garcia A., Lang F., Kim M.H., and Jette M.P. J. Am. Chem. Soc. 116 (1994) 3657-3658
102. Kelly T.R., Silva R.A., Silva H.D., Jasmin S., and Zhao Y. J. Am. Chem. Soc. 122 (2000) 6935-6949
103. Godinez C.E., Zepeda G., and Garcia-Garibay M.A. J. Am. Chem. Soc. 124 (2002) 4701-4707
104. Annunziata R., Benaglia M., Cinquini M., Raimondi L., and Cozzi F. J. Phys. Org. Chem. 17 (2004) 749-751
105. Stiles M., and Miller R.G. J. Am. Chem. Soc. 82 (1960) 3802
106. Friedman L., and Logullo F.M. J. Am. Chem. Soc. 85 (1963) 1549
107. Burckhardt U., Hintermann L., Schnyder A., and Togni A. Organometallics 14 (1995) 5415-5425
108. Franklin E.C. Chem. Rev. 16 (1935) 305-361
109. Bergstrom F.W. Chem. Rev. 35 (1944) 77-277
110. Lichtenthaler F.W. Acc. Chem. Res. 35 (2002) 728-737
111. Litvinov V.P. Russ. Chem. Rev. 72 (2003) 69-85
112. Xu Y., and Guo Q.-X. Heterocycles 63 (2004) 903-974
113. Padwa A., and Waterson A.G. Curr. Org. Chem. 4 (2000) 175-203
114. Orru R.V.A., and de Greef M. Synthesis (2003) 1471-1499
115. Kirsch G., Hesse S., and Comel A. Curr. Org. Chem. 1 (2004) 47-63
116. Yamashita Y., Hayashi T., and Masumura M. Chem. Lett. (1980) 1133-1136
117. Compagnini A., Lo Vullo A., Chiacchio U., Corsaro A., and Purrello G. J. Heterocycl. Chem. 19 (1982) 641-643
118. Atanes N., Guitian E., Saa C., Castedo L., and Saa J.M. Tetrahedron Lett. 28 (1987) 817-820
119. Al-Rawi J.M.A., and Khayat M.A.R. Magn. Reson. Chem. 27 (1989) 112-116
120. Agawa C., Otsuka K., Minoura M., Mazaki Y., and Yamamoto G. Bull. Chem. Soc. Jpn. 77 (2004) 2273-2281
121. CrystalStructure 3.7.0: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC; 9009 New Trails Dr.: The Woodlands, TX 77381, USA, 2000-2005.
122. Watkin D.J., Prout C.K., Carruthers J.R., and Betteridge P.W. CRYSTALS Issue 10 (1996), Chemical Crystallography Laboratory, Oxford, UK