Highly Enantioselective Allylic C-H Alkylation of Terminal Olefins with Pyrazol-5-ones Enabled by Cooperative Catalysis of Palladium Complex and Brønsted Acid

Journal of the American Chemical Society

Volumn 138, Issue 43, 2016, Pages 14354-14361

  Lin, Hua Chen ^a   Wang, Pu Sheng ^a   Tao, Zhong Lin ^a   Chen, Yu Gen ^a   Han, Zhi Yong ^a   Gong, Liu Zhu ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b Chemical Engineering Research Center   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBON; CATALYSIS; LIGANDS; PALLADIUM COMPOUNDS; PHOSPHORIC ACID; STEREOSELECTIVITY;

ALKYLATION REACTIONS; CHIRAL PALLADIUM COMPLEXES; CLASSICAL TRANSFORMATION; COOPERATIVE CATALYSIS; HIGH ENANTIOSELECTIVITY; PALLADIUM COMPLEXES; PALLADIUM-CATALYZED; STEREOGENIC CENTERS;

ENANTIOSELECTIVITY;

ALKENE; ALLYL COMPOUND; BRONSTED ACID; CARBON; HYDROGEN; PALLADIUM COMPLEX; PHOSPHORIC ACID; PYRAZOLONE; QUINONE DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; HYDROGEN BOND; OXIDATION; SUBSTITUTION REACTION;

EID: 84994275270     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b08236     Document Type: Article

References (99)

1. Trost, B. M. Science 1991, 254, 1471 10.1126/science.1962206
2. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259 10.1002/anie.199502591
3. Fuji, K. Chem. Rev. 1993, 93, 2037 10.1021/cr00022a005
4. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5363 10.1073/pnas.0307113101
5. Trost, B. M.; Jiang, C. Synthesis 2006, 369 10.1055/s-2006-926302
6. Wang, B.; Tu, Y. Acc. Chem. Res. 2011, 44, 1207 10.1021/ar200082p
7. Quasdorf, K. W.; Overman, L. E. Nature 2014, 516, 181 10.1038/nature14007
8. Hayashi, T. J. Organomet. Chem. 1999, 576, 195 10.1016/S0022-328X(98)01058-4
9. Helmchen, G. J. Organomet. Chem. 1999, 576, 203 10.1016/S0022-328X(98)01059-6
10. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1 10.1248/cpb.50.1
11. Trost, B. M. J. Org. Chem. 2004, 69, 5813 10.1021/jo0491004
12. Trost, B. M.; Machacek, M. R.; Aponick, A. Acc. Chem. Res. 2006, 39, 747 10.1021/ar040063c
13. Rios, I. G.; Rosas-Hernandez, A.; Martin, E. Molecules 2011, 16, 970 10.3390/molecules16010970
14. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387 10.1016/S0040-4039(00)71674-1
15. Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292 10.1021/ja00782a080
16. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395 10.1021/cr9409804
17. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921 10.1021/cr020027w
18. Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659 10.1021/ar020153m
19. Lu, Z.; Ma, S. M. Angew. Chem., Int. Ed. 2008, 47, 258 10.1002/anie.200605113
20. Bandini, M. Angew. Chem., Int. Ed. 2011, 50, 994 10.1002/anie.201006522
21. Bandini, M.; Cera, G.; Chiarucci, M. Synthesis 2012, 44, 504 10.1055/s-0031-1289681
22. Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467 10.1039/c2cs35024f
23. Jensen, T.; Fristrup, P. Chem.-Eur. J. 2009, 15, 9632 10.1002/chem.200901935
24. Liu, G.; Wu, Y. Top. Curr. Chem. 2009, 292, 195 10.1007/128-2009-16
25. Engelin, C. J.; Fristrup, P. Molecules 2011, 16, 951 10.3390/molecules16010951
26. Li, B. J.; Shi, Z. J. Chem. Soc. Rev. 2012, 41, 5588 10.1039/c2cs35096c
27. Liron, F.; Oble, J.; Lorion, M. M.; Poli, G. Eur. J. Org. Chem. 2014, 2014, 5863 10.1002/ejoc.201402049
28. Mann, S. E.; Benhamou, L.; Sheppard, T. D. Synthesis 2015, 47, 3079 10.1055/s-0035-1560465
29. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56 10.1021/ja056541b
30. Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901 10.1021/ja803452p
31. Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090 10.1021/ja806867p
32. Young, A. J.; White, M. C. Angew. Chem., Int. Ed. 2011, 50, 6824 10.1002/anie.201101654
33. Trost, B. M.; Hansmann, M. M.; Thaisrivongs, D. A. Angew. Chem., Int. Ed. 2012, 51, 4950 10.1002/anie.201200601
34. Howell, J. M.; Liu, W.; Young, A. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 5750 10.1021/ja500726e
35. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242 10.1039/b816707a
36. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215 10.1021/cr100280d
37. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780 10.1021/cr100379j
38. Zheng, C.; You, S. L. RSC Adv. 2014, 4, 6173 10.1039/c3ra46996d
39. Denney, D. B.; Napier, R.; Cammarata, A. J. Org. Chem. 1965, 30, 3151 10.1021/jo01020a066
40. Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831 10.1016/0040-4039(95)00140-8
41. Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945 10.1016/0040-4039(95)00444-H
42. Kawasaki, K.; Tsumura, S.; Katsuki, T. Synlett 1995, 1995, 1245 10.1055/s-1995-5260
43. Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806 10.1021/ja026266i
44. Zhang, B.; Zhu, S.-F.; Zhou, Q.-L. Tetrahedron Lett. 2013, 54, 2665 10.1016/j.tetlet.2013.03.046
45. El-Qisiari, A. K.; Qaseer, H. A.; Henry, P. M. Tetrahedron Lett. 2002, 43, 4229 10.1016/S0040-4039(02)00749-9
46. Covell, D. J.; White, M. C. Angew. Chem., Int. Ed. 2008, 47, 6448 10.1002/anie.200802106
47. Du, H. F.; Zhao, B. G.; Shi, Y. J. Am. Chem. Soc. 2008, 130, 8590 10.1021/ja8027394
48. Takenaka, K.; Akita, M.; Tanigaki, Y.; Takizawa, S.; Sasai, H. Org. Lett. 2011, 13, 3506 10.1021/ol201314m
49. Wang, P.-S.; Liu, P.; Zhai, Y.-J.; Lin, H.-C.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 12732 10.1021/jacs.5b08477
50. Trost, B. M.; Thaisrivongs, D. A.; Donckele, E. J. Angew. Chem., Int. Ed. 2013, 52, 1523 10.1002/anie.201207870
51. Trost, B. M.; Donckele, E. J.; Thaisrivongs, D. A.; Osipov, M.; Masters, J. T. J. Am. Chem. Soc. 2015, 137, 2776 10.1021/jacs.5b00786
52. Wang, P.-S.; Lin, H.-C.; Zhai, Y.-J.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 12218 10.1002/anie.201408199
53. Mariappan, G.; Saha, B. P.; Bhuyan, N. R.; Bharti, P. R.; Kumar, D. J. Adv. Pharm. Technol. Res. 2010, 1, 260
54. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. J. Med. Chem. 2007, 50, 5053 10.1021/jm070688r
55. Ebner, S.; Wallfisch, B.; Andraos, J.; Aitbaev, I.; Kiselewsky, M.; Bernhardt, P. V.; Kollenz, G.; Wentrup, C. Org. Biomol. Chem. 2003, 1, 2550 10.1039/B304070D
56. Gogoi, S.; Zhao, C.-G.; Ding, D. Org. Lett. 2009, 11, 2249 10.1021/ol900538q
57. Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2010, 352, 827 10.1002/adsc.200900764
58. Yang, Z.; Wang, Z.; Bai, S.; Liu, X.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 596 10.1021/ol102804p
59. Wang, Z.; Chen, Z.; Bai, S.; Li, W.; Liu, X.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2012, 51, 2776 10.1002/anie.201109130
60. Wang, Z.; Chen, Z.-L.; Bai, S.; Li, W.; Liu, X.-H.; Lin, L.-L.; Feng, X.-M. Angew. Chem., Int. Ed. 2012, 51, 2776 10.1002/anie.201109130
61. Li, F.; Sun, L.; Teng, Y.; Yu, P.; Zhao, C.-G.; Ma, J.-A. Chem.-Eur. J. 2012, 18, 14255 10.1002/chem.201202636
62. Chauhan, P.; Mahajan, S.; Enders, D. Chem. Commun. 2015, 51, 12890 10.1039/C5CC04930J
63. Tao, Z.-L.; Zhang, W.-Q.; Chen, D.-F.; Adele, A.; Gong, L.-Z. J. Am. Chem. Soc. 2013, 135, 9255 10.1021/ja402740q
64. Chen, G.; Deng, Y.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567 10.1016/S0957-4166(01)00276-2
65. Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329 10.1021/ol016567h
66. Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302 10.1039/b309033g
67. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222 10.1021/ar700133y
68. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745 10.1039/b901258n
69. Allen, A. E.; Macmillan, D. W. Chem. Sci. 2012, 3, 633 10.1039/c2sc00907b
70. Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337 10.1039/C2CS35258C
71. Chen, D.-F.; Han, Z.- Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365 10.1021/ar500101a
72. Alper, H.; Hamel, N. J. Am. Chem. Soc. 1990, 112, 2803 10.1021/ja00163a053
73. Chai, Z.; Rainey, T.-J. J. Am. Chem. Soc. 2012, 134, 3615 10.1021/ja2102407
74. Yu, S.-Y.; Zhang, H.; Gao, Y.; Mo, L.; Wang, S.; Yao, Z.-J. J. Am. Chem. Soc. 2013, 135, 11402 10.1021/ja405764p
75. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336 10.1021/ja074678r
76. Jiang, G.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471 10.1002/anie.201103263
77. Tao, Z.-L.; Li, X.-H.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 4054 10.1021/jacs.5b00507
78. Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. Organometallics 1993, 12, 1790 10.1021/om00029a040
79. Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176 10.1021/ja506036q
80. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70 10.1021/ja9726522
81. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346 10.1021/ar990084k
82. Minnaard, A. J.; Feringa, B. L.; Lefort, L.; De Vries, J. G. Acc. Chem. Res. 2007, 40, 1267 10.1021/ar7001107
83. Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486 10.1002/anie.200904948
84. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566 10.1002/anie.200353240
85. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356 10.1021/ja0491533
86. Terada, M. Synthesis 2010, 2010, 1929 10.1055/s-0029-1218801
87. Akiyama, T. Chem. Rev. 2007, 107, 5744 10.1021/cr068374j
88. Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2009, 291, 395 10.1007/128-2009-1
89. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156 10.1021/ar2000343
90. Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem. Rev. 2014, 114, 9047 10.1021/cr5001496
91. Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603 10.1038/nchem.1405
92. Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534 10.1002/anie.201205449
93. Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518 10.1002/anie.201205343
94. Prétôt, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323 10.1002/(SICI)1521-3773(19980216)37:3<323::AID-ANIE323>3.0.CO;2-T
95. Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681 10.1021/ja973150r
96. You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471 10.1021/ja016121w
97. Jeffery, T. Tetrahedron Lett. 1992, 33, 1989 10.1016/0040-4039(92)88121-K
98. Brown, H. C.; Liotta, R.; Kramer, G. W. J. Org. Chem. 1978, 43, 1058 10.1021/jo00400a007
99. Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Sato, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314 10.1021/ja00183a048