Palladium(II)-catalyzed domino reaction of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles: Scope, mechanism and synthetic application in the synthesis of 3,4-fused bicyclic tetrasubstituted furans

Advanced Synthesis and Catalysis

Volumn 351, Issue 4, 2009, Pages 617-629

  Xiao, Yuanjing ^a   Zhang, Junliang ^a,b  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Cyclization; Domino reactions; Fused ring systems; Palladium; Synthetic methods

Indexed keywords

EID: 62549125065     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800715     Document Type: Article

References (128)

1. a) M. V. Sargent, F. M. Dean, in: Comprehensive Heterocyclic Chemistry, Vol. 4, (Eds.: A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp 599-656;
2. D. M. X. Donnelly, M. J. Meegan, in: Comprehensive Heterocyclic Chemistry, Vol. 4, (Eds. : A. R. Katrizky, C. W. Rees), Pergamon Press, New York, 1984, pp 657-712;
3. b) Natural Products Chemistry, (Ed.: K. Nakanishi), Kodansha, Toyko, 1974, pp 392-403;
4. c) M. Shipman, Contemp. Org. Synth. 1995, 2, 1.
5. G. Vernin, in: Chemistry of Heterocyclic Compounds in Flavours and Aromas, (Ed.: G. Vernin), Ellis Horwood, Chichester, 1982, pp 74-85;
6. G. Vernin, C. Parknanyi, in: Chemistry of Heterocyclic Compounds in Flavours and Aromas, (Ed.: G. Vernin), Ellis Horwood, Chichester, 1982, pp 161-165.
7. a) B. H. Lipshutz, Chem. Rev. 1986, 86, 795;
8. b) R. Benassi, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon: Oxford, 1996; Vol. 2, pp 259-295;
9. c) H. Heaney, J. S. Ahn, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, Vol. 2, pp 297-357;
10. d) W. Friedrichsen, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996; Vol. 2, pp 351-393;
11. e) B. A. Keay, P. W. Dibble, in: Comprehensive Heterocyclic Chemistry II, (Eds. : A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, Vol. 2, pp 395-436;
12. f) Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991.
13. a) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, John Wiley, New York, 1989;
14. b) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
15. For reviews, see: a) X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y.T. Tong, H.N. C. Wong, Tetrahedron 1998, 54, 1955;
16. b) B. A. Keay, Chem. Soc. Rev. 1999, 28, 209;
17. c) T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2849;
18. d) S. Cacchi, J. Organomet. Chem. 1999, 576, 42;
19. e) X. L. Hou, Z. Yang, K. S. Yeung, H. N. C. Wong, in: Progress in Heterocyclic Chemistry, Vol. 19, (Eds.: G. W. Gribble, J. A. Joule), Pergamon, Oxford, 2008, p 176;
20. f) S. F. Kirsch, Org. Biomol. Chem. 2006, 4, 2076.
21. a) J. A. Marshall, E. D. Robinson, J. Org. Chem. 1990, 55, 3450;
22. b) J. A. Marshall, G. S. Bartley, J. Org. Chem. 1994, 59, 7169;
23. c) J. A. Marshall, E. M. Wallace, J. Org. Chem. 1995, 60, 796;
24. d) A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749;
25. Angew. Chem. Int. Ed. Engl. 1995, 34, 1581;
26. e) A. S. K. Hashmi, T. L. Ruppert, T. Knofel, J. W. Bats, J. Org. Chem. 1997, 62, 7295;
27. f) A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382;
28. Angew. Chem. Int. Ed. 2000, 39, 2285;
29. g) S. Ma, L. Li, Org. Lett. 2000, 2, 941;
30. h) S. Ma, Z. Yu, Angew. Chem. 2002, 114,1853;
31. Angew. Chem. Int. Ed. 2002, 41, 1775;
32. i) S. Ma, ; J. Zhang, L. Lu, Chem. Eur. J. 2003, 9, 2447;
33. j) J. T. Kim, A. V. Kel'in, V. Gevorgyan, Angew. Chem. 2003, 115, 102;
34. Angew. Chem. Int. Ed. 2003, 42, 98;
35. k) A. W. Sromek, A. V. Kel'in, V. Gevorgyan, Angew. Chem. 2004, 116, 2330;
36. Angew. Chem. Int. Ed. 2004, 43, 2280;
37. l) M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett. 2005, 7, 3925;
38. m) A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 10500;
39. n) A. Dudnik, V. Gevorgyan, Angew. Chem. 2007, 119, 5287;
40. Angew. Chem. Int. Ed. 2007, 46, 5195;
41. o) T. Schwier, A.W. Sromek, D. M. L. Yap, D. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 9868.
42. a) Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, J. Org. Chem. 1991, 56, 5816;
43. b) A. V. Kel'in, V. Gevorgyan, J. Org. Chem. 2002, 67, 95.
44. J. Zhang, H. G. Schmalz, Angew. Chem. 2006, 118, 6856;
45. Angew. Chem. Int. Ed. 2006, 45, 6704.
46. Y. H. Liu, F. Song, Z. Song, M. Liu, ; B. Yan, Org. Lett. 2005, 7, 5409.
47. a) S. Ma, J. Zhang, Angew. Chem. 2003, 115, 193;
48. Angew. Chem. Int. Ed. 2003, 42, 183;
49. b) S. Ma, L. Lu, J. Zhang, J. Am. Chem. Soc. 2004, 126, 9645.
50. a) A. Padwa, J. M. Kassir, S. L. Xu, J. Org. Chem. 1991, 56, 6971;
51. b) S. Ma, J. Zhang, J. Am. Chem. Soc. 2003, 125, 12386.
52. M. W. Miller, C. R. Johnson, J. Org. Chem. 1997, 62, 1582.
53. T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164.
54. a) N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531;
55. b) C. Oh, V. Reddy, A. Kim, C. Rhim, Tetrahedron Lett. 2006, 47, 5307;
56. c) X. Liu, Z. Pan, X. Shu, X. Duan, Y. Hang, Synlett 2006, 12, 1962.
57. a) Y. H. Liu, S. Zhou, Org. Lett. 2005, 7, 4609;
58. b) T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679.
59. For selected recent examples see: a) R. Sanz, D. Miguel, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriguez, Org. Lett. 2007, 9, 727;
60. b) V. Cadierno, J. Gimeno, N. Nebra, Adv. Synth. Catal, 2007, 349, 382;
61. c) I. Yavari, A. Mokhtarporyani-Sanandaj, L. Morad, A. Mirzaei, Tetrahedron 2008, 64, 5221;
62. d) X. Feng, Z. Tan, D. Chen, Y. Shen, C. Guo, J. Xiang, C. Zhu, Tetrahedron Lett. 2008, 49, 4110;
63. e) Z. Chai, Z. Xie, X. Liu, G. Zhao, J. Wang, J. Org. Chem. 2008, 73, 2947.
64. a) M. Suzuki, H. Ohtaka, Y. Kameya, N. Hamanaka, R. Noyori, J. Org. Chem. 1989, 54, 5292;
65. b) M. E. Price, N. E. Schore, J. Org. Chem. 1989, 54, 2777;
66. c) Y. Siquot, P. Frere, T. Nozdryn, J. Cousseau, M. Salle, M. Jubauct, J. Orduna, J. Carin, A. Corguesa, Tetrahedron Lett, 1997, 38, 1919;
67. d)G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814.
68. 2 acts as both a Lewis acid and a transition metal, see: N. Asao, T. Nogami, K. Takahashi, Y. Yammamoto, J. Am. Chem. Soc. 2002, 124, 764.
69. For recent reviews, see: a) A. Dömling, Curr. Opin. Chem. Biol. 2002, 6, 306;
70. b) R. V. A. Orru, M. de Greef, Synthesis 2003, 1471;
71. c) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51;
72. d) J. Zhu, Eur. J. Org. Chem. 2003, 1133;
73. e) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Ace. Chem. Res. 2003, 36, 899;
74. f) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
75. Angew. Chem. Int. Ed. 2005, 44, 1602;
76. g) A. Dondoni, A. Massi, Acc. Chem. Res. 2006, 39, 451;
77. h) A. Dömling, Chem. Rev. 2006, 106, 17;
78. i) D. M. D'Souza, T.J.J. Müller, Chem. Soc. Rev. 2007, 36, 1095;
79. j) T. J. J. Müller, in: Topics in Organometallic Chemistry (Ed. T. J. J. Müller), Springer, Berlin, 2006, Vol. 19, pp 149;
80. k) Multicomponent Reactions, (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
81. Part of this work has been published in the preliminary communication, see: Y. Xiao, J. Zhang, Angew. Chem. 2008, 120, 1929;
82. Angew. Chem. Int. Ed. 2008, 47, 1903.
83. For reviews, see: a) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137;
84. Angew. Chem. Int. Ed. Engl. 1993, 32, 131;
85. b) R. A. Bunce, Tetrahedron Tetrahedron. 1995, 57, 13103;
86. c) L.F. Tietze, Chem. Rev. 1996, 96, 115;
87. d) S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137;
88. e) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev. 1996, 96, 195;
89. f) H. Pellissier, Tetrahedron 2006, 62, 2143;
90. g) H. Pellissier, Tetrahedron 2006, 62, 1619;
91. h) L. F. Tietze, G. Brasche, K. Gercke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, p 672;
92. i) Metal Catalyzed Cascade Reactions, (Ed: T. J. J. Müller), Springer, Berlin, Heidelberg. Top. Organomet. Chem. 2006, Vol 19;
93. j) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
94. Angew. Chem. Int. Ed. 2006, 45, 7134;
95. k) D. M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36,1095;
96. l) S. F. Kirsch, Synthesis 2008, 3183.
97. The reaction of 2-(1-alkynyl)-2-alken-1-ones with 1, 3-diketones as C-based nucleophiles readily affords 4H-pyrans under basic reaction conditions, see: X. Yu, H. Ren, Y. Xiao, J. Zhang, Chem. Eur. J. 2008, 14, 8481, and unpublished results.
98. int = 0.0199), number of observations [I>2σ(I)] 3289, parameters 288. CCDC 698140 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.
99. S. Ma, B. Xu, Bukuo. Ni, J. Org. Chem. 2000, 65, 8532.
100. For selected recent examples see: a) K. Akiyama, K. Wakabayashi, K. Mikami, Adv. Synth. Catal. 2005, 347,1569;
101. b) K. S. Yoo, C. H. Yoon, R. K. Mishra, Y. C. Jung, S. W. Yi, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384;
102. c) K. S. Yoo, C. P. Park, C. H. Yoon, S. Sakaguchi, J. O'Neill, K. W. Jung, Org. Lett, 2007, 9, 3933;
103. d) For a review, see: E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318.
104. For selected recent examples, see: a) J. D. Crowley, K. D. Hanni, A. L. Lee, D. A. Leigh, J. Am. Chem. Soc. 2007, 129, 12092;
105. b) J. Lindh, P.-A. Enquist, A. Pilotti, P. Nilsson, M. Larhed, J. Org. Chem, 2007, 72, 7957;
106. c) R. Giri, N. Maugel, J. Li, D. Wang, S. Breazzano, L. Saunders, J. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
107. d) C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc. 2008, 130, 1566.
108. For selected recent examples see: a) A. Lei, X. Zhang, Org. Lett, 2002, 4, 2285;
109. b) Y. Zhao, H. Wang, X. Hou, Y. Hu, A. Lei, H. Zhang, L. Zhu, J. Am. Chem. Soc. 2006, 128, 15048;
110. c) Y. Zhao, L. Jin, P. Li, A. Lei, J. Am. Chem. Soc. 2008, 130, 9429.
111. a) C. Liu, X. wang, T. Pei, R. A. Widenhoefer, Chem. Eur. J. 2004, 10, 6343;
112. b) Z. Wang, S. Sugiarti, C. Morales, C. Jensen, D. Morales-Morales, Inorg. Chim. Acta 2006, 359, 1923;
113. c) 14d.
114. W. Liu, Y. Xie, Y. Liang, J. Li, Synthesis 2006, 860.
115. a) J. G. Duboudin, B. Jousseaume, A. Saux, J. Organomet. Chem, 1979, 168, 1;
116. b) M. Frederick Hawthorne, J. Am. Chem. Soc. 1960, 82, 1886.
117. For the Pd-catalyzed allylation-cyclization reactions, see: a) Y. Wakabayashi, Y. Fukuda, H. Shiragami, K. Utimoto, H. Nozaki, Tetrahedron 1985, 41, 3655;
118. b) M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem, 1992, 57, 6377;
119. [6g,7a]
120. See the catalytic cycle of Heck reaction: a) F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2005, 67, 11771;
121. b) S. Brase, A. de. Meijere, Metal-Catalyzed Cross-Coupling Reactions, Wiley, Chichester, 1998, pp 99-166.
122. a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetrahedron. Lett, 1998, 39, 6011;
123. b) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750;
124. c) T. Nishimura, K. Ohe, S. Uemura, J. Am. Chem. Soc. 1999, 121, 2645.
125. For reviews, see: a) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124;
126. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036;
127. b) R. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413.
128. D. J. Faulkner, Nat. Prod. Rep. 1986, 3, 1.