Mechanisms of Brønsted acid catalyzed additions of phenols and protected amines to olefins: A DFT study

European Journal of Organic Chemistry

Volumn , Issue 25, 2008, Pages 4296-4303

  Li, Xin ^a   Ye, Siyu ^a   He, Chuan ^b   Yu, Zhi Xiang ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Alkenes; Br nsted acids; Density functional calculations; Nucleophilic addition; Reaction mechanisms

Indexed keywords

EID: 53849101074     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800337     Document Type: Article

References (69)

1. a) V. Baliah, R. Jeyaraman, L. Chandrasekaran, Chem. Rev. 1983, 83, 379;
2. b) R. R. Schmidt, Acc. Chem. Res. 1986, 19, 250;
3. c) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675;
4. d) M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368;
5. e) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673;
6. f) A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199.
7. For selected recent reports, see: a) A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 6042;
8. b) S. B. Herzon, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 6690;
9. c) Y. Oe, T. Ohta, Y. Ito, Chem. Commun. 2004, 1620;
10. d) J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafer, Org. Lett. 2005, 7, 1959;
11. e) M. R. Crimmin, I. J. Casely, M. S. Hill, J. Am. Chem. Soc. 2005, 127, 2042;
12. f) C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070;
13. g) J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798;
14. h) X. Zhang, A. Corma, Chem. Commun. 2007, 3080;
15. i) J. Michaux, V. Terrasson, S. Marque, J. Wehbe, D. Prim, J.-M. Campagne, Eur. J. Org. Chem. 2007, 2601;
16. j) G. A. Olah, Angew. Chem. Int. Ed. Engl. 1995, 34, 1393;
17. k) Z. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175, and references cited therein;
18. l) K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. Int. Ed. 2006, 45, 2938;
19. for a recent review on gold chemistry and the chemistry of gold-catalyzed nucleophilic additions, see: m) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896.
20. Base-catalyzed hydroamination is also developed, see a review: J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795.
21. a) M. Beller, O. R. Thiel, H. Trauthwein, Synlett 1999, 243;
22. b) B. Schlummer, J. F. Hartwig, Org. Lett. 2002, 4, 1471.
23. L. L. Anderson, J. Arnold, R. G. Bergman, J. Am. Chem. Soc. 2005, 127, 14542.
24. a) K. C. Nicolaou, A. Li, D. J. Edmonds, Angew. Chem. Int. Ed. 2006, 45, 7086.
25. For selected other references, see: a) Q. Wang, Q. Huang, B. Chen, J. Lu, H. Wang, X. She, X. Pan, Angew. Chem. Int. Ed. 2006, 45, 3651;
26. b) R. Heim, S. Wiedemann, C. M. Williams, P. V. Bernhardt, Org. Lett. 2005, 7, 1327.
27. a) J. B. Levy, R. W. Taft, L. P. Hammett, J. Am. Chem. Soc. 1953, 75, 1253;
28. b) A. V. Willi, Helv. Chim. Acta 1964, 47, 647;
29. c) A. V. Willi, Helv. Chim. Acta 1964, 47, 655;
30. d) G. Modena, F. Rivetti, G. Scorrano, U. Tonellato, J. Am. Chem. Soc. 1977, 99, 3392.
31. P. N. Liu, Z. Y. Zhou, C. P. Lau, Chem. Eur. J. 2007, 13, 8610.
32. After submission of this paper, Ackermann and Althammer reported that phosphoric acid can catalyze the intramolecular addition of amines to alkenes. This reaction has been developed to an asymmetric one with low stereoselectivity. For details, see: a) L. Ackermann, A. Althammer, Synlett 2008, 995.
33. For recent reviews on phosphoric acids as catalysts, see: b) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
34. for pioneering works, see: c) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
35. d) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004, 43, 1566;
36. for recent other examples, see: e) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086;
37. f) Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem. Int. Ed. 2007, 46, 5565;
38. g) Q.-X. Guo, H. Liu, C. Guo, S.-W. Luo, Y. Gu, L.-Z. Gong, J. Am. Chem. Soc. 2007, 129, 3790, and references therein.
39. TfOH can coordinate the olefin to form complex 1′, which is also a relatively stable species in the system, but the phenol can further form a hydrogen bond with 1′, leading to the formation of true reactive intermediate 1. See the Supporting Information for details.
40. For a review on addition reactions, see: F. A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry, Brooks/Cole Publishing Company, 1998.
41. For experimental and computational studies on C-H⋯O interactions, see: a) I. Washington, K. N. Houk, Angew. Chem. Int. Ed. 2001, 40, 4485;
42. b) F. M. Raymo, M. D. Bartberger, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 9264;
43. c) E. Arbely, I. T. Arkin, J. Am. Chem. Soc. 2004, 126, 5362;
44. d) H. Matsuura, H. Yoshida, M. Hieda, S.-y. Yamanaka, T. Harada, K. Shin-ya, K. Ohno, J. Am. Chem. Soc. 2003, 125, 13910;
45. e) R. Vargas, J. Garza, D. A. Dixon, B. P. Hay, J. Am. Chem. Soc. 2000, 122, 4750;
46. f) S. Scheiner, T. Kar, Y. Gu, J. Biol. Chem. 2001, 276, 9832.
47. U. Koch, P. L. A. Popelier, J. Phys. Chem. 1995, 99, 9747.
48. P. L. A. Popelier, J. Phys. Chem. A 1998, 102, 1873.
49. For discussions on hydrogen-bond interactions, see: a) L. González, O. Mó, M. Yáñez, J. Phys. Chem. A 1997, 101, 9710;
50. b) L. González, O. Mó, M. Yáñez, J. Comput. Chem. 1997, 18, 1124.
51. -1. Details are given in the Supporting Information.
52. For recent theoretical studies on protonation and carbocations, see: a) P. Gutta, D. J. Tantillo, Org. Lett. 2007, 9, 1069;
53. b) R. Ponec, P. Bultinck, P. Gutta, D. J. Tantillo, J. Phys. Chem. A 2006, 110, 3785;
54. c) P. Gutta, D. J. Tantillo, J. Am. Chem. Soc. 2006, 128, 6172;
55. d) M. Jacobsson, J. Oxgaard, C.-O. Abrahamsson, P.-O. Norrby, W. A. Goddard III, U. Ellervik, Chem. Eur. J. 2008, 14, 3954.
56. For the addition of phenol to the terminal olefin, the favored reaction pathway is addition to the internal carbon atom and not the terminal carbon atom of the alkene. See the Supporting Information for details.
57. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
58. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
59. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
60. a) K. Fukui, J. Phys. Chem. 1970, 74, 4161;
61. b) K. Fukui, Acc. Chem. Res. 1981, 14, 363;
62. c) C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523.
63. a) M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43;
64. b) J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.
65. a) A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735;
66. b) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
67. a) R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon, Oxford, 1990;
68. b) F. Biegler-König, J. Schönbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545;
69. c) F. Biegler-König, J. Schönbohm, J. Comput. Chem. 2002, 23, 1489.