RhIII-catalyzed oxidative olefination of vinylic C-H bonds: Efficient and selective access to Di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes

Chemistry - A European Journal

Volumn 17, Issue 26, 2011, Pages 7167-7171

  Besset, Tatiana ^a   Kuhl, Nadine ^b   Patureau, Frederic W ^b   Glorius, Frank ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

amino acids; butadienes; C H activation; oxidative Heck coupling; rhodium

Indexed keywords

1 ,3 BUTADIENE; AMINO ACID DERIVATIVES; C-H ACTIVATION; C-H BOND; CROSS-COUPLINGS; OLEFINATION; OXIDATIVE HECK-COUPLING;

ACTIVATION ANALYSIS; BUTADIENE; CATALYSIS; OLEFINS; RHODIUM; STYRENE;

AMINO ACIDS;

1,3 BUTADIENE DERIVATIVE; ALKENE; AMINO ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKENES; AMINO ACIDS; BUTADIENES; CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHODIUM;

EID: 79958782198     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101340     Document Type: Article

References (118)

1. I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119
2. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992
3. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
4. For selected papers concerning intermolecular Pd-catalyzed oxidative olefination reactions, see
5. M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. 2003, 115, 3636
6. Angew. Chem. Int. Ed. 2003, 42, 3512
7. T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476
8. N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. 2005, 117, 3185
9. Angew. Chem. Int. Ed. 2005, 44, 3125
10. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 7666
11. J.-R. Wang, C.-T. Yang, L. Liu, Q.-X. Guo, Tetrahedron Lett. 2007, 48, 5449
12. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
13. J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 2009, 131, 13888
14. A. García-Rubia, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2009, 121, 6633
15. Angew. Chem. Int. Ed. 2009, 48, 6511
16. A. García-Rubia, B. Urones, R. Gómez Arrayás, J. C. Carretero, Chem. Eur. J. 2010, 16, 9676
17. T. Nishikata, B. H. Lipshutz, Org. Lett. 2010, 12, 1972; for a recent review on this topic, see
18. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170; for intramolecular oxidative Heck couplings, see
19. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578
20. H. Zhang, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2004, 116, 6270
21. Angew. Chem. Int. Ed. 2004, 43, 6144
22. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. 2008, 120, 7340
23. Angew. Chem. Int. Ed. 2008, 47, 7230.
24. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586.
25. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. 2008, 120, 6552
26. Angew. Chem. Int. Ed. 2008, 47, 6452
27. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072
28. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315
29. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680
30. B.-F. Shi, Y.-H. Zhang, J. K. Lam, D.-H. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 460
31. K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2010, 122, 6305
32. Angew. Chem. Int. Ed. 2010, 49, 6169.
33. S. Mochida, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 5776
34. N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094
35. S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 6295; See also
36. M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211
37. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407; for a detailed review of this topic, see
38. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
39. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982
40. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
41. Angew. Chem. Int. Ed. 2011, 50, 1064
42. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350; See also
43. S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585
44. F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154.
45. For other examples of Rh-catalyzed oxidative olefination reactions, see
46. T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Catal. 2002, 206, 272
47. A. S. Tsai, M. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540
48. A. S. Tsai, M. E. Tauchert, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 1248
49. Y. Li, B.-J. Li, W.-H. Wang, W.-P. Huang, X.-S. Zhang, K. Chen, Z.-J. Shi, Angew. Chem. 2011, 123, 2163
50. Angew. Chem. Int. Ed. 2011, 50, 2115.
51. For selected examples of vinylic C-H functionalization reactions, see
52. T. Sato, F. Kakiuchi, N. Chatani, S. Murai, Chem. Lett. 1998, 893
53. C.-H. Jun, C. W. Moon, Y.-M. Kim, H. Lee, J. H. Lee, Tetrahedron Lett. 2002, 43, 4233
54. D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2006, 128, 5604
55. L. J. Gooßen, N. Rodríguez, Angew. Chem. 2007, 119, 7688
56. Angew. Chem. Int. Ed. 2007, 46, 7544
57. A. S. Tsai, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 6316
58. K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325
59. R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082
60. M.-O. Simon, R. Martinez, J.-P. Genêt, S. Darses, Adv. Synth. Catal. 2009, 351, 153, and references therein
61. N. M. Neisius, B. Plietker, Angew. Chem. 2009, 121, 5863
62. Angew. Chem. Int. Ed. 2009, 48, 5752
63. Y. Shibata, Y. Otake, M. Hirano, K. Tanaka, Org. Lett. 2009, 11, 689
64. M.-O. Simon, J.-P. Genêt, S. Darses, Org. Lett. 2010, 12, 3038
65. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
66. Y. Su, M. Zhao, K. Han, G. Song, X. Li, Org. Lett. 2010, 12, 5462
67. D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 3645
68. A. T. Lindhardt (neé Hansen), M. L. H. Mantel, T. Skrydstrup, Angew. Chem. 2008, 120, 2708
69. Angew. Chem. Int. Ed. 2008, 47, 2668
70. J.-P. Ebran, A. L. Hansen, T. M. Gøgsig, T. Skrydstrup, J. Am. Chem. Soc. 2007, 129, 6931
71. A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skrydstrup, Angew. Chem. 2006, 118, 3427; Angew. Chem. Int. Ed. 2006, 45, 3349
72. Angew. Chem. Int. Ed. 2006, 45, 3349
73. see, reference [5c].
74. For the Pd-catalyzed synthesis of dienes, see
75. Y. Hatamoto, S. Sakaguchi, Y. Ishii, Org. Lett. 2004, 6, 4623
76. Y.-H. Xu, J. Lu, T.-P. Loh, J. Am. Chem. Soc. 2009, 131, 1372
77. Y.-H. Xu, W.-J. Wang, Z.-K. Wen, J. J. Hartley, T.-P. Loh, Tetrahedron Lett. 2010, 51, 3504
78. H. Yu, W. Jin, C. Sun, J. Chen, W. Du, S. He, Z. Yu, Angew. Chem. 2010, 122, 5928
79. Angew. Chem. Int. Ed. 2010, 49, 5792
80. W. Al-Maksoud, L. Djakovitch, M. Jahjah, C. Pinel, Sci. China Chem. 2010, 53, 1927.
81. For selected papers dealing with the preparation of 1,3-butadienes, see
82. E.-I. Negishi, Z. Huang, G. Wang, S. Mohan, C. Wang, H. Hattori, Acc. Chem. Res. 2008, 41, 1474, and references therein
83. M. Yamashita, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 592; for their application in Diels-Alder reactions, see
84. K. C. Nicolaou, S. S. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742
85. Angew. Chem. Int. Ed. 2002, 41, 1668
86. A. Deagostino, C. Prandi, C. Zavattaro, P. Venturello, Eur. J. Org. Chem. 2006, 2463; for selected examples of diene structures in natural products, see
87. A. B. Smith III, I. G. Safonov, R. M. Corbett, J. Am. Chem. Soc. 2002, 124, 11102
88. T. R. Hoye, M. Hu, J. Am. Chem. Soc. 2003, 125, 9576
89. F. Ding, M. P. Jennings, Org. Lett. 2005, 7, 2321.
90. M. J. Burk, J. G. Allen, W. F. Kiesman, J. Am. Chem. Soc. 1998, 120, 657, and references therein
91. M. J. Burk, J. G. Allen, W. F. Kiesman, K. M. Stoffan, Tetrahedron Lett. 1997, 38, 1309.
92. 2) leading to the corresponding amino acid derivative 9 a in 97 % yield and 99 % ee.
93. A trace of a third diastereomer is barely detectable (<5 %).
94. Examples of powerful C-H activations utilizing acetanilides as substrates
95. V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156
96. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 7416
97. Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 5650
98. Angew. Chem. Int. Ed. 2007, 46, 5554
99. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474
100. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
101. T. Nishikata, A. R. Abela, S. Huang, B. H. Lipshutz, J. Am. Chem. Soc. 2010, 132, 4978
102. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
103. R. Giri, J. K. Lam, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 686.
104. In the cases of N-(1-phenyl-vinyl)-acetamide and N-vinylacetamide, complete degradation of the starting materials was observed. (Z)-N-Acetyl dehydrophenylalanine methyl ester, however, did not react.
105. Subjecting product 4 a to the standard reaction conditions (Scheme 1) did not alter the E/Z ratio, suggesting that isomerization occurs during product formation. See reference [22].
106. The corresponding cyclic compound 4 b′ with a Z-configuration exclusively was obtained as a by-product in 12 % isolated yield.
107. For the use of 7 a in asymmetric organocatalysis, see:, T. Jousseaume, N. E. Wurz, F. Glorius, Angew. Chem. 2011, 123, 1446
108. Angew. Chem. Int. Ed. 2011, 50, 1410.
109. III-catalyzed C-H bond functionalization of alkenes (especially enamide 7 a) with internal alkynes, leading to pyrroles appeared
110. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
111. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374
112. Angew. Chem. Int. Ed. 2011, 50, 1338.
113. 2, DCE, 120 °C, 16 h. Compound 10 b was obtained starting from 8 b, 10 c from 8 a (Scheme 2). Compound 10 f is drawn as the main regioisomer, the yield of the minor one (10 g) is indicated in brackets; see the Supporting Information.
114. When ethylene was used as partner, only oligomers were detected. Mono- and di-substituted aliphatic olefins, that is, 3,3-dimethyl-1-butene or cyclohexene, yield only traces of product under the reaction conditions.
115. See the Supporting Information.
116. 2] was used as a precursor, only starting material was recovered.
117. The two proposed pathways are illustrated by the following equations
118. A Friedel-Crafts type mechanism involving the condensation of the olefin onto 7 a can be excluded as even electron-poor butylacrylate reacts towards 8 l in good yield. Furthermore, 4-methoxystyrene did not lead to any product formation.