Bifunctional Ligand-Assisted Catalytic Ketone α-Alkenylation with Internal Alkynes: Controlled Synthesis of Enones and Mechanistic Studies

Journal of the American Chemical Society

Volumn 137, Issue 49, 2015, Pages 15518-15527

  Mo, Fanyang ^a,b   Lim, Hee Nam ^a   Dong, Guangbin ^a  

^a University of Texas at Austin   (United States)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLATION; CHELATION; KETONES; LIGANDS; ORGANIC POLYMERS; REACTION INTERMEDIATES; RHODIUM;

BIFUNCTIONAL LIGAND; CONTROL EXPERIMENTS; CONTROLLED SYNTHESIS; DEUTERIUM LABELING; MECHANISTIC STUDIES; REACTION CONDITIONS; SUBSTITUTED ALKENE; UNSATURATED KETONES;

HYDROCARBONS;

ALCOHOL DERIVATIVE; ALKENE; ALKYNE; AMIDE; DEUTERIUM; ENAMINE; ESTER; KETONE; LIGAND; MALONIC ACID DERIVATIVE; RHODIUM;

ALKYLATION; ALPHA ALKENYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CRYSTAL STRUCTURE; DEFENSE MECHANISM; DERIVATIZATION; MASS SPECTROMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84950265651     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10466     Document Type: Article

References (99)

1. Escher, I.; Glorious, F. Sci. Synth. 2007, 25, 733
2. Radin, N. S. Drug Dev. Res. 2008, 69, 15 10.1002/ddr.20223
3. Patai, S.; Rappoport, Z., Eds. The Chemistry of Enones; John Wiley & Sons: New York, 1989; Vols. 1 and 2.
4. Buckle, D. R.; Pinto, I. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 7, pp 119-149.
5. Larock, R. C. Comprehensive Organic Transformations; John Wiley & Sons: New York, 1999; pp 251-256.
6. Dénès, F.; Pérez-Luna, A.; Chemla, F. Chem. Rev. 2010, 110, 2366 10.1021/cr800420x
7. Huang, Z.; Lim, H. N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764
8. Patil, N. T.; Kavthe, R. D.; Shinde, V. S. Tetrahedron 2012, 68, 8079 10.1016/j.tet.2012.05.125
9. Bloch, R.; Le Perchec, P.; Conia, J. M. Tetrahedron 1968, 24, 5971 10.1016/S0040-4020(01)90982-2
10. Conia, J. M.; Le Perchec, P. Synthesis 1975, 1975, 1 10.1055/s-1975-23652
11. Drouin, J.; Leyendecker, F.; Conia, J. M. Tetrahedron 1980, 36, 1203 10.1016/0040-4020(80)87019-0
12. Mandville, G.; Conia, J. M. Nouv. J. Chim. 1981, 5, 137
13. Boaventura, M. A.; Drouin, J.; Conia, J. M. Synthesis 1983, 1983, 801 10.1055/s-1983-30519
14. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526 10.1021/ja049487s
15. Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350 10.1002/anie.200460844
16. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486 10.1021/ja066800c
17. Ito, H.; Makida, Y.; Ochida, A.; Ohmiya, H.; Sawamura, M. Org. Lett. 2008, 10, 5051 10.1021/ol802079r
18. Pan, J.-H.; Yang, M.; Gao, Q.; Zhu, N.-Y.; Yang, D. Synthesis 2007, 2007, 2539 10.1055/s-2007-983804
19. Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185 10.1021/ol050532q
20. Deng, C.-L.; Song, R.-J.; Liu, Y.-L.; Li, J.-H. Adv. Synth. Catal. 2009, 351, 3096 10.1002/adsc.200900588
21. Deng, C.-L.; Zou, T.; Wang, Z.-Q.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2009, 74, 412 10.1021/jo802133w
22. Montel, S.; Bouyssi, D.; Balme, G. Adv. Synth. Catal. 2010, 352, 2315 10.1002/adsc.201000351
23. Deng, C.-L.; Song, R.-J.; Guo, S.-M.; Wang, Z.-Q.; Li, J.-H. Org. Lett. 2007, 9, 5111 10.1021/ol7023289
24. Liu, Y.; Song, R.-J.; Li, J.-H. Synthesis 2010, 2010, 3663 10.1055/s-0030-1258213
25. Davies, P. W.; Detty-Mambo, C. Org. Biomol. Chem. 2010, 8, 2918 10.1039/c003473h
26. Chernyak, N.; Gorelsky, S. I.; Gevorgyan, V. Angew. Chem., Int. Ed. 2011, 50, 2342 10.1002/anie.201006751
27. Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168 10.1021/ja055059q
28. Yang, T.; Ferrali, A.; Sladojevich, F.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 9140 10.1021/ja9004859
29. Matsuzawa, A.; Mashiko, T.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2011, 50, 7616 10.1002/anie.201102114
30. Phillips, E. M.; Roberts, J. M.; Scheidt, K. A. Org. Lett. 2010, 12, 2830 10.1021/ol100938j
31. Tsuji, H.; Yamagata, K.-i.; Itoh, Y.; Endo, K.; Nakamura, M.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 8060 10.1002/anie.200702928
32. Nakamura, M.; Nakamura, E.; Itoh, Y.; Tsuji, H.; Yamagata, K.; Endo, K.; Tanaka, I. J. Am. Chem. Soc. 2008, 130, 17161 10.1021/ja805657h
33. Tsuji, H.; Yamagata, K.-i.; Fujimoto, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 7792 10.1021/ja8015186
34. Peng, W.; Lee, C.-S. Synlett 2008, 2008, 142 10.1055/s-2007-990953
35. Jackson, W. P.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1981, 1516 10.1039/p19810001516
36. McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691 10.1016/S0040-4039(97)10007-7
37. Chan, L. Y.; Kim, S.; Park, Y.; Lee, P. H. J. Org. Chem. 2012, 77, 5239 10.1021/jo300957q
38. Shaw, S.; White, J. D. J. Am. Chem. Soc. 2014, 136, 13578 10.1021/ja507853f
39. Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002 10.1021/ja038006m
40. Nakamura, M.; Endo, K.; Nakamura, E. Org. Lett. 2005, 7, 3279 10.1021/ol051057z
41. Nakamura, M.; Endo, K.; Nakamura, E. Adv. Synth. Catal. 2005, 347, 1681 10.1002/adsc.200505206
42. Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823 10.1021/ol0515208
43. Nakamura, M. Pure Appl. Chem. 2006, 78, 425 10.1351/pac200678020425
44. Endo, K.; Hatakeyama, T.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 5264 10.1021/ja0702014
45. Tsuji, H.; Fujimoto, T.; Endo, K.; Nakamura, N.; Nakamura, E. Org. Lett. 2008, 10, 1219 10.1021/ol800105r
46. Fujimoto, T.; Endo, K.; Tsuji, H.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 4492 10.1021/ja710408f
47. Kuninobu, Y.; Nishi, M.; Yudha, S.; Takai, K. Org. Lett. 2008, 10, 3009 10.1021/ol800969h
48. Tsuji, H.; Tanaka, I.; Endo, K.; Yamagata, K.-i.; Nakamura, M.; Nakamura, E. Org. Lett. 2009, 11, 1845 10.1021/ol9003542
49. Onodera, G.; Kato, M.; Kawano, R.; Kometani, Y.; Takeuchi, R. Org. Lett. 2009, 11, 5038 10.1021/ol9020095
50. Murahashi, S.; Naota, T.; Nakano, Y. Synlett 2009, 20, 3355 10.1055/s-0029-1218373
51. Cheung, H. W.; So, C. M.; Pun, K. H.; Zhou, Z.; Lau, C. P. Adv. Synth. Catal. 2011, 353, 411 10.1002/adsc.201000567
52. Pennington-Boggio, M. K.; Conley, B. L.; Williams, T. J. J. J. Organomet. Chem. 2012, 716, 6 10.1016/j.jorganchem.2012.05.017
53. Xi, Y.; Wang, D.; Ye, X.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Org. Lett. 2014, 16, 306 10.1021/ol403337u
54. Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362 10.1021/ja00061a058
55. Yamaguchi, M.; Sehata, M.; Hayashi, A.; Hirama, M. J. Chem. Soc., Chem. Commun. 1993, 1708 10.1039/c39930001708
56. Hayashi, Y.; Yamaguchi, M.; Hirama, M. Synlett 1995, 1995, 51 10.1055/s-1995-4877
57. Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074 10.1021/ja984022l
58. Trofimov, B. A.; Schmidt, E. Y.; Ushakov, I. A.; Zorina, N. V.; Skital'tseva, E. V.; Protsuk, N. I.; Mikhaleva, A. b. I. Chem.-Eur. J. 2010, 16, 8516 10.1002/chem.201000227
59. Trofimov, B. A.; Schmidt, E. Y.; Zorina, N. V.; Ivanova, E. V.; Ushakov, I. A. J. Org. Chem. 2012, 77, 6880 10.1021/jo301005p
60. For a preliminary report of our ketone-olefin couplings, see: Mo, F.; Dong, G. Science 2014, 345, 68 10.1126/science.1254465
61. Park, Y.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222 10.1021/ar700133y
62. Kitamura, T. Eur. J. Org. Chem. 2009, 2009, 1111 10.1002/ejoc.200801054
63. Wang, X.; Zhou, L.; Lu, W. Curr. Org. Chem. 2010, 14, 289 10.2174/138527210790231964
64. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814 10.1021/ar200190g
65. Yang, L.; Huang, H. Chem. Rev. 2015, 115, 3468 10.1021/cr500610p
66. Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1980, 507 10.1246/cl.1980.507
67. Yamazaki, H.; Hong, P. J. Mol. Catal. 1983, 21, 133 10.1016/0304-5102(93)80116-C
68. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681 10.1246/cl.1995.681
69. Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371 10.1021/ja00124a025
70. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385 10.1021/om00007a045
71. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 24, 681 10.1246/cl.1995.681
72. Dürr, U.; Kisch, H. Synlett 1997, 12, 1335 10.1055/s-1997-1035
73. Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609 10.1016/S0040-4039(01)01618-5
74. Jun, C.-H.; Lee, H.; Hong, J.-B.; Kwon, B.-I. Angew. Chem., Int. Ed. 2002, 41, 2146 10.1002/1521-3773(20020617)41:12<2146::AID-ANIE2146>3.0.CO;2-2
75. Kakiuchi, F.; Uetsuhara, T.; Tanaka, Y.; Chatani, N.; Murai, S. J. Mol. Catal. A: Chem. 2002, 182, 511 10.1016/S1381-1169(01)00500-3
76. Jun, C.-H.; Lee, H.; Hong, J.-B.; Kwon, B.-I. Angew. Chem., Int. Ed. 2002, 41, 2146 10.1002/1521-3773(20020617)41:12<2146::AID-ANIE2146>3.0.CO;2-2
77. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 5604 10.1021/ja0584931
78. Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.-K.; Endo, K.; Shibata, T. J. Organomet. Chem. 2008, 693, 3939 10.1016/j.jorganchem.2008.09.065
79. Katagiri, T.; Mukai, T.; Satoh, T.; Hirano, K.; Miura, M. Chem. Lett. 2009, 38, 118 10.1246/cl.2009.118
80. Schipper, D. J.; Hutchinson, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6910 10.1021/ja103080d
81. Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2010, 132, 12249 10.1021/ja106814p
82. Kanyiva, K. S.; Kashihara, N.; Nakao, Y.; Hiyama, T.; Ohashi, M.; Ogoshi, S. Dalton Trans. 2010, 39, 10483 10.1039/c0dt00104j
83. Lee, P.-S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 17283 10.1021/ja2047073
84. Nakao, Y.; Morita, E.; Idei, H.; Hiyama, T. J. Am. Chem. Soc. 2011, 133, 3264 10.1021/ja1102037
85. Ito, J.-i.; Kitase, M.; Nishiyama, H. Organometallics 2007, 26, 6412 10.1021/om700742t
86. Katagiri, T.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Commun. 2008, 3405 10.1039/b804573a
87. Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M. J. Org. Chem. 2011, 76, 13 10.1021/jo1021184
88. For a recent seminal work on selective hydrolysis of conjugated enamines, see: Duttwyler, S.; Chen, S.; Takase, M. K.; Wiberg, K. B.; Bergman, R. G.; Ellman, J. A. Science 2013, 339, 678 10.1126/science.1230704
89. For a similar regioselectivity observed on C-H/alkyne couplings, see: Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645 10.1021/ja7104784
90. Sánchez, D.; Bastida, D.; Burés, J.; Isart, C.; Pineda, O.; Vilarrasa, J. Org. Lett. 2012, 14, 536 10.1021/ol203157s
91. Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728 10.1021/ja00270a036
92. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624 10.1021/cr900005n
93. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507 10.1038/417507a
94. Wang, Z.; Reinus, B. J.; Dong, G. J. Am. Chem. Soc. 2012, 134, 13954 10.1021/ja306123m
95. Wang, Z.; Reinus, B. J.; Dong, G. Chem. Commun. 2014, 50, 5230 10.1039/C3CC47556E
96. Cheng, C.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 12064 10.1021/ja505844k
97. Sevov, C. S.; Zhou, J.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 3200 10.1021/ja412116d
98. Feller, M.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2013, 135, 11040 10.1021/ja401852c
99. Mague, J. T.; Wilkinson, G. J. Chem. Soc. A 1966, 1736 10.1039/j19660001736