Reasons Two Nonstrained C-C σ-Bonds Can Be Easily Cleaved in Decyanative [4 + 2] Cycloaddition Catalyzed by Nickel(0)/Lewis Acid Systems. Theoretical Insight

ACS Catalysis

Volumn 5, Issue 1, 2015, Pages 1-10

  Guan, Wei ^a,b   Sakaki, Shigeyoshi ^a   Kurahashi, Takuya ^c   Matsubara, Seijiro ^c  

^a KYOTO UNIVERSITY   (Japan)

^b NORTHEAST NORMAL UNIVERSITY   (China)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

C C bond activation; density functional theory calculation; Lewis acid; nickel complex; synergy effect

Indexed keywords

ATOMS; CARBON; CHEMICAL ACTIVATION; CHEMICAL BONDS; HYDROCARBONS; NICKEL; ORGANOMETALLICS; OXYGEN;

C-C BOND ACTIVATION; CARBONYL OXYGEN ATOMS; ELECTROPHILIC NATURES; LEWIS ACID; NICKEL COMPLEX; REDUCTIVE ELIMINATION; SYNERGY EFFECT; [4 + 2] CYCLOADDITION;

DENSITY FUNCTIONAL THEORY;

EID: 84927947002     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501653s     Document Type: Article

References (101)

1. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759 - 1792 10.1021/cr960118r
2. Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610 - 618 10.1039/b308864m
3. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300 - 307 10.1039/b702940n
4. Bonesi, S. M.; Fagnoni, M. Chem. Eur. J. 2010, 16, 13572 - 13589 10.1002/chem.201001478
5. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100 - 1105 10.1039/c0cc02566f
6. Ruhland, K. Eur. J. Org. Chem. 2012, 2683 - 2706 10.1002/ejoc.201101616
7. Trost, B. M. Science 1991, 254, 1471 - 1477 10.1126/science.1962206
8. Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373 - 2381 10.1021/ja00059a036
9. Sakaki, S.; Mizoe, N.; Musashi, Y.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027 - 8036 10.1021/jp981899y
10. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870 - 883 10.1002/(SICI)1521-3773(19990401)38:7<870::AID-ANIE870>3.0.CO;2-3
11. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117 - 3179 10.1021/cr050988l
12. Matsuda, T.; Shigeno, M.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 12086 - 12087 10.1021/ja075141g
13. Seiser, T.; Roth, O. A.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 6320 - 6323 10.1002/anie.200903189
14. Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340 - 5341 10.1021/ja101469t
15. Lin, M.; Li, F.; Jiao, L.; Yu, Z.-X. J. Am. Chem. Soc. 2011, 133, 1690 - 1693 10.1021/ja110039h
16. Thakur, A.; Facer, M. E.; Louie, J. Angew. Chem., Int. Ed. 2013, 52, 12161 - 12165 10.1002/anie.201306869
17. Masarwa, A.; Didier, D.; Zabrodski, T.; Schinkel, M.; Ackermann, L.; Marek, I. Nature 2014, 505, 199 - 203 10.1038/nature12761
18. Chen, P.-H.; Xu, T.; Dong, G.-B. Angew. Chem., Int. Ed. 2014, 53, 1674 - 1678 10.1002/anie.201310100
19. Souillart, L.; Parker, E.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 3001 - 3005 10.1002/anie.201311009
20. Fisher, E. L.; Lampert, T. H. Org. Lett. 2009, 11, 4108 - 4110 10.1021/ol901598n
21. Youn, S. W.; Kim, B. S.; Jagdale, A. R. J. Am. Chem. Soc. 2012, 134, 11308 - 11311 10.1021/ja304616q
22. Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412 - 413 10.1021/ja8066308
23. Sattler, A.; Parkin, G. Nature 2010, 463, 523 - 526 10.1038/nature08730
24. Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244 - 15247 10.1021/ja205228y
25. Gooßen, L. J.; Deng, G.-J.; Levy, L. M. Science 2006, 313, 662 - 664 10.1126/science.1128684
26. Cicchillo, R. M.; Zhang, H.-J.; Blodgett, J. A. V.; Whitteck, J. T.; Li, G.-Y.; Nair, S. K.; van der Donk, W. A.; Metcalf, W. W. Nature 2009, 459, 871 - 874 10.1038/nature07972
27. Shang, R.; Fu, Y.; Li, J.-B.; Zhang, S.-L.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738 - 5739 10.1021/ja900984x
28. Pusterla, I.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 513 - 516 10.1002/anie.201107198
29. Kajita, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2008, 130, 17226 - 17227 10.1021/ja806569h
30. He, C.; Guo, S.; Huang, L.; Lei, A.-W. J. Am. Chem. Soc. 2010, 132, 8273 - 8275 10.1021/ja1033777
31. Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573 - 13576 10.1021/ja306062c
32. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982 - 15989 10.1021/ja804992n
33. Tobisu, M.; Kinuta, H.; Kita, Y.; Rémond, E.; Chatani, N. J. Am. Chem. Soc. 2012, 134, 115 - 118 10.1021/ja2095975
34. Shi, Y. L.; Roth, K. E.; Ramgren, S. D.; Blum, S. A. J. Am. Chem. Soc. 2009, 131, 18022 - 18023 10.1021/ja9068497
35. Liu, X.; Henderson, J. A.; Sasaki, T.; Kishi, Y. J. Am. Chem. Soc. 2009, 131, 16678 - 16680 10.1021/ja9079308
36. Trost, B. M.; Luan, X. J. J. Am. Chem. Soc. 2011, 133, 1706 - 1709 10.1021/ja110501v
37. Mustard, T. J. L.; Mack, D. J.; Njardarson, J. T.; Cheong, P. H.-Y. J. Am. Chem. Soc. 2013, 135, 1471 - 1475 10.1021/ja310065z
38. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222 - 234 10.1021/ar700133y
39. Shao, Z.-H.; Zhang, H.-B. Chem. Soc, Rev. 2009, 38, 2745 - 2755 10.1039/b901258n
40. Yeung, C. S.; Dong, V.-M. Angew. Chem., Int. Ed. 2011, 50, 809 - 812 10.1002/anie.201006489
41. Quintard, A.; Alexakis, A.; Mazet, C. Angew. Chem., Int. Ed. 2011, 50, 2354 - 2358 10.1002/anie.201007001
42. Skucas, E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 9090 - 9093 10.1021/ja303116v
43. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094 - 8097 10.1021/ja3030164
44. Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065 - 1068 10.1126/science.1237068
45. Burns, N. Z.; Written, M. R.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578 - 14581 10.1021/ja206997e
46. Mittal, N.; Sun, D.-X.; Seidel, D. Org. Lett. 2012, 14, 3084 - 3087 10.1021/ol301155b
47. Min, C.; Mittal, N.; De, C. K.; Seidel, D. Chem. Commun. 2012, 48, 10853 - 10855 10.1039/c2cc36361e
48. Rueping, M.; Volla, C. M. R.; Atodiresei, I. Org. Lett. 2012, 14, 4642 - 4645 10.1021/ol302084q
49. Wang, C.-Y.; Xi, Z.-F. Chem. Soc. Rev. 2007, 36, 1395 - 1406 10.1039/b608694m
50. Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627 - 3641 10.1021/ja037002e
51. Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428 - 2429 10.1021/ja067364x
52. Nakao, Y.; Hirata, Y.; Tannaka, M.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 385 - 387 10.1002/anie.200704095
53. Nakao, Y.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874 - 12875 10.1021/ja805088r
54. Nakao, Y.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2010, 132, 10024 - 10026 10.1021/ja1017078
55. Hirata, Y.; Yada, A.; Morita, E.; Nakao, Y.; Hiyama, T.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2010, 132, 10070 - 10077 10.1021/ja102346v
56. Minami, Y.; Yoshiyasu, H.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2013, 52, 883 - 887 10.1002/anie.201207880
57. Watson, M. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 12594 - 12595 10.1021/ja805094j
58. Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452 - 2456 10.1002/anie.200805601
59. Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2011, 133, 11066 - 11068 10.1021/ja203829j
60. Nakai, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2013, 15, 856 - 859 10.1021/ol303546p
61. Nakazawa, H.; Kawasaki, T.; Miyoshi, K.; Suresh, C. H.; Koga, N. Organometallics 2004, 23, 117 - 126 10.1021/om0208319
62. Nakazawa, H.; Kamata, K.; Itazaki, M. Chem. Commun. 2005, 4004 - 4006 10.1039/b504131g
63. Li, X.-Y.; Sun, H.-J.; Yu, F.-L.; Flörke, U.; Klein, H.-F. Organometallics 2006, 25, 4695 - 4697 10.1021/om060572d
64. Xu, H.-W.; Williard, P. G.; Bernskoetter, W. H. Organometallics 2012, 31, 1588 - 1590 10.1021/om201270n
65. Garcia, J. J.; Jones, W. D. Organometallics 2000, 19, 5544 - 5545 10.1021/om0008474
66. Garcia, J. J.; Brunkan, N. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 9547 - 9555 10.1021/ja0204933
67. García, J. J.; Arévalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997 - 4002 10.1021/om049700t
68. Ateşin, T. A.; Li, T.; Lachaize, S.; Brennessel, W. W.; García, J. J.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 7562 - 7569 10.1021/ja0707153
69. Ateşin, T. A.; Li, T.; Lachaize, S.; García, J. J.; Jones, W. D. Organometallics 2008, 27, 3811 - 3817 10.1021/om800424s
70. Ohnishi, Y.-Y.; Nakao, Y.; Sato, H.; Sakaki, S. J. Phys. Chem. A 2007, 111, 7915 - 7924 10.1021/jp071816q
71. Ohnishi, Y.-Y.; Nakao, Y.; Sato, H.; Nakao, Y.; Hiyama, T.; Sakaki, S. Organometallics 2009, 28, 2583 - 2594 10.1021/om8008525
72. Marlin, D. S.; Olmstead, M. M.; Mascharak, P. K. Angew. Chem., Int. Ed. 2001, 40, 4752 - 4754 10.1002/1521-3773(20011217)40:24<4752::AID-ANIE4752>3.0.CO;2-L
73. Lu, T.-B.; Zhuang, X.-M.; Li, Y.-W.; Chen, S. J. Am. Chem. Soc. 2004, 126, 4760 - 4761 10.1021/ja031874z
74. Churchill, D.; Shin, J. H.; Hascall, T.; Hahn, J. M.; Bridgewater, B. M.; Parkin, G. Organometallics 1999, 18, 2403 - 2406 10.1021/om990195n
75. Ochiai, M.; Hashimoto, H.; Tobita, H. Angew. Chem., Int. Ed. 2007, 46, 8192 - 8194 10.1002/anie.200703154
76. Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2002, 124, 4192 - 4193 10.1021/ja0255094
77. Taw, F. L.; Mellows, H.; White, P. S.; Hollander, F. J.; Bergman, R. G.; Brookhart, M.; Heinekey, D. M. J. Am. Chem. Soc. 2002, 124, 5100 - 5108 10.1021/ja0165990
78. Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808 - 9813 10.1021/ja034468o
79. Evans, M. E.; Jones, W. D. Organometallics 2011, 30, 3371 - 3377 10.1021/om2002602
80. Liu, Q.-X.; Xu, F.-B.; Li, Q.-S.; Song, H.-B.; Zhang, Z.-Z. Organometallics 2004, 23, 610 - 614 10.1021/om034183k
81. Anand, M.; Sunoj, R. B. Org. Lett. 2012, 14, 4584 - 4587 10.1021/ol302047c
82. Pham, H. V.; Paton, R. S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2397 - 2403 10.1021/ja410220w
83. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215 - 241 10.1007/s00214-007-0310-x
84. Guan, W.; Sakaki, S.; Kurahashi, T.; Matsubara, S. Organometallics 2013, 32, 7564 - 7574 10.1021/om401061s
85. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995 10.1021/jp9716997
86. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669 10.1002/jcc.10189
87. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999 - 3093 10.1021/cr9904009
88. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299 - 310 10.1063/1.448975
89. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359 - 1370 10.1002/(SICI)1096-987X(199608)17:11<1359::AID-JCC9>3.0.CO;2-L
90. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111 - 114 10.1016/0009-2614(93)80086-5
91. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866 - 872 10.1063/1.452288
92. Martin, J. M. L.; Sundermann, A. J. Chem. Phys. 2001, 114, 3408 - 3420 10.1063/1.1337864
93. Mammen, M.; Shakhnovich, E. I.; Deutch, J. M.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3821 - 3830 10.1021/jo970944f
94. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01; Gaussian, Inc., Wallingford, CT, 2009.
95. A 3 molar equiv amount of LA molecules would be necessary for coordination equilibrium and interaction with free substrate.
96. Guan, W.; Sayyed, F. B.; Zeng, G.; Sakaki, S. Inorg. Chem. 2014, 33, 6444 - 6457 10.1021/ic5003429
97. Sayyed, F. B.; Tsuji, Y.; Sakaki, S. Chem. Commun. 2013, 49, 10715 - 10717 10.1039/c3cc45836a
98. Even starting from an assumed nickel(II) intermediate 2d-LA2 with a d bond distance of 2.39 Å, the geometry optimization leads to the stable η2-coordinated nickel(0) complex 1d-LA2 (see Figure 3).
99. Baba, H.; Suzuki, S.; Takemura, T. J. Chem. Phys. 1969, 50, 2078 - 2086 10.1063/1.1671336
100. Kato, S.; Yamabe, S.; Fukui, K. J. Chem. Phys. 1974, 60, 572 - 578 10.1063/1.1681075
101. Dapprich, S.; Frenking, G. J. Phys. Chem. 1995, 99, 9352 - 9362 10.1021/j100023a009