Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations

Angewandte Chemie - International Edition

Volumn 53, Issue 37, 2014, Pages 9931-9935

  Burns, David J ^a   Lam, Hon Wai ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

C H functionalization; catalysis; enyne; oxidation; rhodium

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; OXIDATION; RHODIUM;

1 ,4-MIGRATION; ALLYLIC HYDROGEN; C-H ACTIVATION; C-H FUNCTIONALIZATION; ENYNE; FUNCTIONALIZATIONS; OXIDATIVE ANNULATION; RHODIUM-CATALYZED;

CARBON;

EID: 84906949039     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201406072     Document Type: Article

References (109)

1. For selected reviews covering directing-group-assisted metal-catalyzed C-H functionalizations, see
2. K. M. Engle, J.-Q. Yu, J. Org. Chem. 2013, 78, 8927-8955
3. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788-802
4. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292
5. J. Wencel-Delord, T. Droege, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740-4761
6. L. Ackermann, Chem. Rev. 2011, 111, 1315-1345
7. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677-685
8. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169
9. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624-655.
10. For a review of rhodium-catalyzed oxidative annulation of alkynes and alkenes, see:, T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212-11222.
11. For a review of ruthenium-catalyzed oxidative annulation of alkynes, see:, L. Ackermann, Acc. Chem. Res. 2014, 47, 281-295.
12. For representative recent examples of metal-catalyzed oxidative annulations of alkynes that result in heterocycles, see
13. L. Wang, L. Ackermann, Org. Lett. 2013, 15, 176-179
14. J. Li, L. Neuville, Org. Lett. 2013, 15, 1752-1755
15. N. Quiñones, A. Seoane, R. Garcia-Fandino, J. L. Mascareñas, M. Gulías, Chem. Sci. 2013, 4, 2874-2879
16. S. Ding, Y. Yan, N. Jiao, Chem. Commun. 2013, 49, 4250-4252
17. R. Kuram, M. Bhanuchandra, A. K. Sahoo, Angew. Chem. 2013, 125, 4705-4710
18. Angew. Chem. Int. Ed. 2013, 52, 4607-4612
19. M. C. Reddy, R. Manikandan, M. Jeganmohan, Chem. Commun. 2013, 49, 6060-6062
20. K. Muralirajan, C.-H. Cheng, Chem. Eur. J. 2013, 19, 6198-6202
21. D. Zhao, Q. Wu, X. Huang, F. Song, T. Lv, J. You, Chem. Eur. J. 2013, 19, 6239-6244
22. G. Zhang, L. Yang, Y. Wang, Y. Xie, H. Huang, J. Am. Chem. Soc. 2013, 135, 8850-8853
23. W. Dong, L. Wang, K. Parthasarathy, F. Pan, C. Bolm, Angew. Chem. 2013, 125, 11787-11790
24. Angew. Chem. Int. Ed. 2013, 52, 11573-11576
25. M.-N. Zhao, Z.-H. Ren, Y.-Y. Wang, Z.-H. Guan, Org. Lett. 2014, 16, 608-611
26. A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 834-837
27. Y. Hoshino, Y. Shibata, K. Tanaka, Adv. Synth. Catal. 2014, 356, 1577-1585
28. M. Fukui, Y. Hoshino, T. Satoh, M. Miura, K. Tanaka, Adv. Synth. Catal. 2014, 356, 1638-1644
29. J. Li, L. Ackermann, Tetrahedron 2014, 70, 3342-3348.
30. For examples of metal-catalyzed oxidative annulations of alkynes that result in carbocycles, see
31. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. 2008, 120, 4083-4086
32. Angew. Chem. Int. Ed. 2008, 47, 4019-4022
33. Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697-6703
34. Z. Shi, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 8035-8038
35. Angew. Chem. Int. Ed. 2009, 48, 7895-7898
36. Z. Shi, C. Tang, N. Jiao, Adv. Synth. Catal. 2012, 354, 2695-2700
37. X. Tan, B. Liu, X. Li, B. Li, S. Xu, H. Song, B. Wang, J. Am. Chem. Soc. 2012, 134, 16163-16166
38. S. Reddy Chidipudi, I. Khan, H. W. Lam, Angew. Chem. 2012, 124, 12281-12285
39. Angew. Chem. Int. Ed. 2012, 51, 12115-12119
40. J. D. Dooley, S. Reddy Chidipudi, H. W. Lam, J. Am. Chem. Soc. 2013, 135, 10829-10836
41. J. Nan, Z. Zuo, L. Luo, L. Bai, H. Zheng, Y. Yuan, J. Liu, X. Luan, Y. Wang, J. Am. Chem. Soc. 2013, 135, 17306-17309
42. S. Peng, T. Gao, S. Sun, Y. Peng, M. Wu, H. Guo, J. Wang, Adv. Synth. Catal. 2014, 356, 319-324
43. M. V. Pham, N. Cramer, Angew. Chem. Int. Ed. 2014, 53, 3484-3487
44. S. Kujawa, D. Best, D. J. Burns, H. W. Lam, Chem. Eur. J. 2014, 20, 8599-8602
45. A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc. 2014, 136, 7607-7610.
46. For examples of oxidative annulations of 1,3-enynes, see
47. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374-1377
48. Angew. Chem. Int. Ed. 2011, 50, 1338-1341
49. L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. 2011, 123, 6503-6506
50. Angew. Chem. Int. Ed. 2011, 50, 6379-6382.
51. For examples of one-carbon oxidative annulation partners in catalytic C-H functionalizations that are not alkynes, see Ref. [5g] and
52. M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. 1997, 1103-1104
53. Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916-5921
54. Y. Du, T. K. Hyster, T. Rovis, Chem. Commun. 2011, 47, 12074-12076
55. C. Zhu, W. Xie, J. R. Falck, Chem. Eur. J. 2011, 17, 12591-12595
56. S. Reddy Chidipudi, M. D. Wieczysty, I. Khan, H. W. Lam, Org. Lett. 2013, 15, 570-573
57. T. K. Hyster, K. E. Ruhl, T. Rovis, J. Am. Chem. Soc. 2013, 135, 5364-5367
58. C. Suzuki, K. Morimoto, K. Hirano, T. Satoh, M. Miura, Adv. Synth. Catal. 2014, 356, 1521-1526
59. J. Li, M. John, L. Ackermann, Chem. Eur. J. 2014, 20, 5403-5408
60. B. Ye, N. Cramer, Angew. Chem. Int. Ed. 2014, Early View, DOI:.
61. Y. Ikeda, K. Takano, S. Kodama, Y. Ishii, Chem. Commun. 2013, 49, 11104-11106
62. Y. Ikeda, K. Takano, M. Waragai, S. Kodama, N. Tsuchida, K. Takano, Y. Ishii, Organometallics 2014, 33, 2142-2145.
63. For an example of 1,4-palladium migration to give an allylpalladium(II) species, see:, J. Zhao, M. Campo, R. C. Larock, Angew. Chem. 2005, 117, 1907-1909
64. Angew. Chem. Int. Ed. 2005, 44, 1873-1875.
65. K. Oguma, M. Miura, T. Satoh, M. Nomura, J. Am. Chem. Soc. 2000, 122, 10464-10465
66. T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 2001, 123, 9918-9919.
67. S. Ma, Z. Gu, Angew. Chem. 2005, 117, 7680-7685
68. Angew. Chem. Int. Ed. 2005, 44, 7512-7517
69. F. Shi, R. C. Larock, Top. Curr. Chem. 2010, 292, 123-164.
70. For selected, recent examples of 1,4-rhodium migration, see
71. R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 2071-2073
72. T. Miura, T. Sasaki, H. Nakazawa, M. Murakami, J. Am. Chem. Soc. 2005, 127, 1390-1391
73. R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872-2873
74. H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248-3249
75. R. Shintani, K. Takatsu, T. Hayashi, Angew. Chem. 2007, 119, 3809-3811
76. Angew. Chem. Int. Ed. 2007, 46, 3735-3737
77. T. Matsuda, M. Shigeno, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12086-12087
78. R. Shintani, K. Takatsu, T. Katoh, T. Nishimura, T. Hayashi, Angew. Chem. 2008, 120, 1469-1471
79. Angew. Chem. Int. Ed. 2008, 47, 1447-1449
80. J. Panteleev, F. Menard, M. Lautens, Adv. Synth. Catal. 2008, 350, 2893-2902
81. T. Seiser, O. A. Roth, N. Cramer, Angew. Chem. 2009, 121, 6438-6441
82. Angew. Chem. Int. Ed. 2009, 48, 6320-6323
83. M. Shigeno, T. Yamamoto, M. Murakami, Chem. Eur. J. 2009, 15, 12929-12931
84. R. Shintani, S. Isobe, M. Takeda, T. Hayashi, Angew. Chem. 2010, 122, 3883-3886
85. Angew. Chem. Int. Ed. 2010, 49, 3795-3798
86. T. Seiser, N. Cramer, Angew. Chem. 2010, 122, 10361-10365
87. Angew. Chem. Int. Ed. 2010, 49, 10163-10167
88. K. Sasaki, T. Hayashi, Tetrahedron: Asymmetry 2012, 23, 373-380
89. T. Matsuda, Y. Suda, A. Takahashi, Chem. Commun. 2012, 48, 2988-2990
90. K. Sasaki, T. Nishimura, R. Shintani, E. A. B. Kantchev, T. Hayashi, Chem. Sci. 2012, 3, 1278-1283.
91. For reviews covering rhodium-catalyzed allylic substitutions, see
92. M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2002, 35, 48-58
93. P. A. Evans, in Modern Rhodium-Catalyzed Organic Reactions, Wiley-VCH, Weinheim, 2005.
94. For selected, recent examples of rhodium-catalyzed allylic substitutions, see
95. G. C. Tsui, M. Lautens, Angew. Chem. 2012, 124, 5496-5500
96. Angew. Chem. Int. Ed. 2012, 51, 5400-5404
97. J. Zhu, G. C. Tsui, M. Lautens, Angew. Chem. 2012, 124, 12519-12522
98. Angew. Chem. Int. Ed. 2012, 51, 12353-12356
99. J. S. Arnold, H. M. Nguyen, J. Am. Chem. Soc. 2012, 134, 8380-8383
100. P. A. Evans, E. A. Clizbe, M. J. Lawler, S. Oliver, Chem. Sci. 2012, 3, 1835-1838
101. P. A. Evans, S. Oliver, J. Chae, J. Am. Chem. Soc. 2012, 134, 19314-19317
102. P. A. Evans, S. Oliver, Org. Lett. 2013, 15, 5626-5629
103. J. S. Arnold, E. T. Mwenda, H. M. Nguyen, Angew. Chem. 2014, 126, 3762-3766
104. Angew. Chem. Int. Ed. 2014, 53, 3688-3692.
105. 3 had a detrimental effect.
106. The E:Z stereochemistries of products 11 h and 11 i were determined on the basis of nOe experiments. See the Supporting Information for details.
107. The structure of 13 e was confirmed by X-ray crystallography. CCDC 1006281 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.
108. I migration, which is generally considered to proceed by an oxidative addition-reductive elimination sequence. For example, see Refs. [11a] and [13o].
109. The experiment in Equation (4) also demonstrates that C-H functionalization of the 4-nitrophenyl ring of 1 g is irreversible in the presence of 2 a. Exposure of 1 g to the conditions shown in Equation (4) but in the absence of 2 a led to partial deuterium incorporation (28 % D) at the ortho-positions of the 4-nitrophenyl ring, showing that C-H functionalization of 1 g is reversible when the 1,3-enyne is not present. See the Supporting Information for details.