Nickel-catalyzed alkyl coupling reactions: Evaluation of computational methods

Journal of Physical Chemistry A

Volumn 115, Issue 11, 2011, Pages 2281-2290

  Pratt, Lawrence M ^a   Voit, Stewart ^a   Okeke, Fabian N ^a   Kambe, Nobuaki ^b  

^a FISK UNIVERSITY   (United States)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; CCSD; COUPLING REACTION; DFT METHOD; EVALUATION OF COMPUTATIONAL METHODS; FUNCTIONALS; GROUND STATE GEOMETRY; NICKEL CATALYST; NICKEL CATALYZED COUPLING; NICKEL COMPLEX; NUCLEOPHILIC ATTACK; RATE DETERMINING STEP; REDUCTIVE ELIMINATION; SINGLE-POINT ENERGY; TRANSITION STATE;

ALKYLATION; CATALYSIS; CATALYSTS; PARAFFINS;

NICKEL;

EID: 79952749373     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp1077196     Document Type: Article

References (32)

1. Li, P.; Arikan, F.; Ahlbrecht, W.; Dieckmann, M.; Menche, D. J. Org. Chem. 2010, 75, 2429-2444
2. Zhang, X.; Lu, Z.; Fu, C.; Ma, S. J. Org. Chem. 2010, 75, 2589-2598
3. Bonazzi, S.; Binaghi, M.; Fellay, C.; Wach, J.-Y.; Gademann, K. Synthesis 2010, 631-642
4. Bischop, M.; Doum, V.; Nordschild, A. C. M.; Pietruszka, J.; Sandkuhl, D. Synthesis 2010, 527-537
5. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; De Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
6. Phapale, V. B.; Cardenas, D. J. Chem. Soc. Rev. 2009, 38, 1598-1607
7. Rudolph, A.; Lautens, M. Angew. Che. Int. Ed. 2009, 48, 2656-2670
8. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688
9. Furstner, A.; Martin, R. Chem. Lett. 2005, 34, 624-629
10. Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525-1532
11. Hayashi, T. J. Organomet. Chem. 2002, 653, 41-45
12. Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 8347-8349
13. Node, M.; Ozeki, M.; Planas, L.; Nakano, M.; Takita, H.; Mori, D.; Tamatani, S.; Kajimoto, T. J. Org. Chem. 2010, 75, 190-196
14. Yoo, K. S.; O'Neill, J.; Sakaguchi, S.; Giles, R.; Lee, J. H.; Jung, K. W. J. Org. Chem. 2010, 75, 95-101
15. Recent reviews. For Fe: Sherry, B. D.; Fuerstner, A. Acc. Chem. Res. 2008, 41, 1500-1511 For Co: Gosmini, C.; Begouin, J.-M.; Moncomble, A. Chem. Commun. 2008, 3221-3233 For Ag: Someya, H.; Yorimitsu, H.; Oshima, K. Tetrahedron Lett. 2009, 50, 3270-3272
16. Terao, J.; Watanabe, H.; Ikkumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222-4223
17. Pratt, L. M.; Voit, S.; Mai, B. K.; Nguyen, B. H. J. Phys. Chem. A 2010, 114, 5005-5015
18. Ashby, E. C.; Coleman, D. J. Org. Chem. 1987, 52, 4554-4565
19. Yoshikai, N.; Iida, R.; Nakamura, E. Adv. Synth. Catal. 2008, 350, 1063-1072
20. Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 12264-12265
21. Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293
22. Terao, J.; Kambe, N. Acc. Chem. Res. 2008, 41, 1545-1554
23. Singh, S. P.; Terao, J.; Kambe, N. Tetrahedron Lett. 2009, 50, 5644-5646
24. Gonzales-Bobes, F.; Fu, G. C J. Am. Chem. Soc. 2006, 128, 5360-5361
25. Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556-3558
26. 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; 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, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
27. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
28. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
29. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975
30. The original aug-cc-pvdz basis set in Gaussian 09 had an error that affected the first-row transition metals. That error has been corrected in revision B1, but it is necessary to add the diffuse functions using the general basis set option. They are available for download at http://tyr0.chem.wsu.edu/ ∼kipeters/basissets/tm3dbasis.html. A sample input file is included in the Supporting Information.
31. Pratt, L. M.; Tran, P. T. T.; Nguyen, N. V.; Ramachandran, B. Bull. Chem. Soc. Jpn. 2007, 9, 1107-1125
32. Ramachandran, B.; Kharidehal, P.; Pratt, L. M.; Voit, S.; Okeke, F. N.; Ewan, M. J. Phys. Chem. A 2010, 114, 8423-8433