A general synthesis of ynones from aldehydes via oxidative C-C bond cleavage under aerobic conditions

Journal of the American Chemical Society

Volumn 136, Issue 35, 2014, Pages 12233-12236

  Wang, Zhaofeng ^a   Li, Li ^a   Huang, Yong ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; AMINE; BIOLOGICAL PRODUCT; GOLD; IODIDE; OXYGEN;

CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; ALKYNES; AMINES; BIOLOGICAL PRODUCTS; CATALYSIS; GOLD; IODIDES; OXIDATION-REDUCTION; OXYGEN;

EID: 84906879111     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja506352b     Document Type: Article

References (103)

1. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745
2. Hashmi, A. S. K.; Hubbert, C. Angew. Chem., Int. Ed. 2010, 49, 1010
3. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999
4. Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633
5. Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211
6. Han, Z.-Y.; Wang, C.; Gong, L.-Z. In Science of Synthesis: Asymmetric Organocatalysis; Maruoka, K., Ed.; Georg Thieme Verlag: Stuttgart, 2012; Vol. 2, p 697.
7. Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337
8. Bishop, K. C., III. Chem. Rev. 1976, 76, 461
9. Crabtree, R. H. Chem. Rev. 1985, 85, 245
10. Murakami, M.; Ito, Y. Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; p 97.
11. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870
12. Crabtree, R. H. Nature 2000, 408, 415
13. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610
14. Horino, Y. Angew. Chem., Int. Ed. 2007, 46, 2144
15. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
16. Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100
17. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
18. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300
19. Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452
20. Winter, C.; Krause, N. Angew. Chem., Int. Ed. 2009, 48, 2460
21. Seiser, T.; Cramer, N. Org. Biomol. Chem. 2009, 7, 2835
22. Bonesi, S. M.; Fagnoni, M. Chem.-Eur. J. 2010, 16, 13572
23. Cramer, N.; Seiser, T. Synlett 2011, 449
24. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
25. Ruhland, K. Eur. J. Org. Chem. 2012, 2683
26. Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47, 1137
27. Clennan, E. L.; Heah, P. C. J. Org. Chem. 1981, 46, 4107
28. Kerdesky, F. A. J.; Schmidt, S. P.; Brooks, D. W. J. Org. Chem. 1993, 58, 3516
29. Adlington, R. M.; Baldwin, J. E.; Pritchard, G. J.; Spencer, K. Tetrahedron Lett. 2000, 41, 575
30. Aiguade, J.; Hao, J.; Forsyth, C. J. Org. Lett. 2001, 3, 979
31. Forsyth, C. J.; Xu, J.; Nguyen, S. T.; Samdal, I. A.; Briggs, L. R.; Rundberget, T.; Sandvik, M.; Miles, C. O. J. Am. Chem. Soc. 2006, 128, 15114
32. Nicolaou, K. C.; Sarlah, D.; Shaw, D. M. Angew. Chem., Int. Ed. 2007, 46, 4708
33. Xu, B. H.; Kehr, G.; Fröhlich, R.; Wibbeling, B.; Schirmer, B.; Grimme, S.; Erker, G. Angew. Chem., Int. Ed. 2011, 50, 7183
34. Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277
35. Kelin, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074
36. Jeevanandam, A.; Narkunan, K.; Ling, Y.-C. J. Org. Chem. 2001, 66, 6014
37. Kelin, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95
38. Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. Tetrahedron 2005, 61, 8705
39. Van den Hoven, B. G.; Ali, B. E.; Alper, H. J. Org. Chem. 2000, 65, 4131
40. Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107
41. Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67, 9200
42. Mohamed Ahmed, M. S.; Kobayashi, K.; Mori, A. Org. Lett. 2005, 7, 4487
43. Kirkham, J. D.; Edeson, S. J.; Stokes, S.; Harrity, J. P. Org. Lett. 2012, 14, 5354
44. Hojo, M.; Tomita, K.; Hosomi, A. Tetrahedron Lett. 1993, 34, 485
45. Karpov, A. S.; Müller, T. J. J. Org. Lett. 2003, 5, 3451
46. Karpov, A. S.; Müller, T. J. J. Synthesis 2003, 2815
47. Awuah, E.; Capretta, A. Org. Lett. 2009, 11, 3210
48. Arcadi, A.; Marinelli, F.; Rossi, E. Tetrahedron 1999, 55, 13233
49. Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1961, 83, 2952
50. Maeda, Y.; Kakiuchi, N.; Matsumura, S.; Nishimura, T.; Kawamura, T.; Uemura, S. J. Org. Chem. 2002, 67, 6718
51. Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615
52. Kroeger, J. W.; Nieuwland, J. A. J. Am. Chem. Soc. 1936, 58, 1861
53. Murai, K.; Miyazaki, S.; Fujioka, H. Tetrahedron Lett. 2012, 53, 3746
54. Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679
55. Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 6951
56. DSouza, D. M.; Müller, T. J. J. Nat. Protoc. 2008, 3, 1660
57. Boersch, C.; Merkul, E.; Müller, T. J. J. Angew. Chem., Int. Ed. 2011, 50, 10448
58. Taylor, C.; Bolshan, Y. Org. Lett. 2014, 16, 488
59. Yu, Y.; Yang, W.; Pflästerer, D.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 1144
60. Wang, Z.; Li, X.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 14219
61. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553
62. Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
63. Hashmi, A. S. K.; Lothschütz, C.; Ackermann, M.; Doepp, R.; Anantharaman, S.; Marchetti, B.; Bertagnolli, H.; Rominger, F. Chem.-Eur. J. 2010, 16, 8012
64. Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927
65. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
66. Brand, J. P.; Gonzalez, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102
67. Brand, J. P.; Waser, J. Chem. Soc. Rev. 2012, 41, 4165
68. Nicolai, S.; Piemontesi, C.; Waser, J. Angew. Chem., Int. Ed. 2011, 50, 4680
69. Brand, J. P.; Chevalley, C.; Scopelliti, R.; Waser, J. Chem.-Eur. J. 2012, 18, 5655
70. Brand, J. P.; Waser, J. Org. Lett. 2012, 14, 744
71. Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330
72. Kamlar, M.; Putaj, P.; Veselý, J. Tetrahedron Lett. 2013, 54, 2097
73. Li, Y.; Brand, J. P.; Waser, J. Angew. Chem., Int. Ed. 2013, 52, 6743
74. Aubineau, T.; Cossy, J. Chem. Commun. 2013, 49, 3303
75. Frei, R.; Waser, J. J. Am. Chem. Soc. 2013, 135, 9620
76. González, D. F.; Brand, J. P.; Mondière, R.; Waser, J. Adv. Synth. Catal. 2013, 355, 1631
77. Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2014, 53, 2722
78. Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780
79. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232
80. Vanrheen, V. J. Chem. Soc. D 1969, 3, 314
81. Kaneda, K.; Ito, T.; Kii, N.; Jitsukawa, K.; Teranishi, S. J. Mol. Catal. 1982, 15, 349
82. Ito, T.; Kaneda, K.; Watanabe, I.; Ikeda, S.; Teranishi, S. Chem. Lett. 1976, 227
83. Ebitani, K.; Nagashima, K.; Mizugaki, T.; Kaneda, K. Chem. Commun. 2000, 869
84. Wang, A.; Jiang, H. J. Am. Chem. Soc. 2008, 130, 5030
85. Lu, B.; Shi, M. Chem.-Eur. J. 2011, 17, 9070
86. Celaje, J. A.; Zhang, D.; Guerrero, A. M.; Selke, M. Org. Lett. 2011, 13, 4846
87. Zhang, C.; Xu, Z.; Shen, T.; Wu, G.; Zhang, L.; Jiao, N. Org. Lett. 2012, 14, 2362
88. Haruta, M.; Kobayashi, T.; Sano, H.; Yamada, N. Chem. Lett. 1987, 16, 405
89. Prati, L.; Rossi, M. J. Catal. 1998, 176, 552
90. Comotti, M.; Della Pina, C.; Matarrese, R.; Rossi, M. Angew. Chem., Int. Ed. 2004, 43, 5812
91. Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang, Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005, 127, 18004
92. Cinellu, M. A.; Minghetti, G.; Cocco, F.; Stoccoro, S.; Zucca, A.; Manassero, M. Angew. Chem., Int. Ed. 2005, 44, 6892
93. Liu, Y.; Song, F.; Guo, S. J. Am. Chem. Soc. 2006, 128, 11332
94. Beltrame, P.; Comotti, M.; Della Pina, C.; Rossi, M. Appl. Catal., A 2006, 297, 1
95. Comotti, M.; Della Pina, C.; Falletta, E.; Rossi, M. Adv. Synth. Catal. 2006, 348, 313
96. Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Org. Lett. 2006, 8, 693
97. Hashmi, A. S. K.; Jaimes, M. C. B.; Schuster, A. M.; Rominger, F. J. Org. Chem. 2012, 77, 6394
98. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
99. Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088
100. Su, Y.; Sun, X.; Wu, G.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 9808
101. Sriramurthy, V.; Barcan, G. A.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12928
102. Blitzke, T.; Sicker, D.; Wilde, H. Synthesis 1995, 236
103. Khalaf, A.; Grée, D.; Abdallah, H.; Jaber, N.; Hachem, A.; Grée, R. Tetrahedron 2011, 67, 3881