Guanidines: Highly Nucleophilic Organocatalysts

ChemCatChem

Volumn 4, Issue 7, 2012, Pages 993-999

  Maji, Biplab ^a   Stephenson, David S ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Kinetics; Lewis bases; Linear free energy relationships; Michael addition; Organocatalysis

Indexed keywords

1 ,5 ,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE; LEWIS BASIS; LINEAR FREE ENERGY RELATIONSHIPS; MICHAEL ACCEPTORS; MICHAEL ADDITIONS; NUCLEOPHILICITIES; ORGANOCATALYSIS; ORGANOCATALYSTS; SECOND-ORDER RATE CONSTANTS; TETRAFLUOROBORATES;

ADDITION REACTIONS; ENZYME KINETICS; NUCLEOPHILES; RATE CONSTANTS; REACTION KINETICS;

SELF ASSEMBLY;

EID: 84862730531     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200143     Document Type: Article

References (56)

1. Superbases for Organic Synthesis (Ed.: T. Ishikawa), Wiley, Chichester, 2009.
2. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584-1663; Angew. Chem. Int. Ed. 2008, 47, 1560-1638;
3. N. DeRycke, F. Couty, O. R. P. David, Chem. Eur. J. 2011, 17, 12852-12871;
4. J. E. Taylor, S. D. Bull, J. M. J. Willams, Chem. Soc. Rev. 2012, 41, 2109-2121;
5. T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
6. K. Nagasawa, Y. Hashimoto, Chem. Rec. 2003, 3, 201-211;
7. T. Ishikawa, T. Kumamoto, Synthesis 2006, 737-752;
8. M. P. Coles, Chem. Commun. 2009, 3659-3676;
9. D. Leow, C.-H. Tan, Chem. Asian J. 2009, 4, 488-507;
10. D. Leow, C.-H. Tan, Synlett 2010, 1589-1605;
11. X. Fu, C.-H. Tan, Chem. Commun. 2011, 47, 8210-8222.
12. I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Leito, I. A. Koppel, J. Org. Chem. 2005, 70, 1019-1028.
13. B. G. G. Lohmeijer, R. C. Pratt, F. Leibfarth, J. W. Logan, D. A. Long, A. P. Dove, F. Nederberg, J. Choi, C. Wade, R. M. Waymouth, J. L. Hedrick, Macromolecules 2006, 39, 8574-8583;
14. R. C. Pratt, B. G. G. Lohmeijer, D. A. Long, R. M. Waymouth, J. L. Hedrick, J. Am. Chem. Soc. 2006, 128, 4556-4557;
15. N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G. Lohmeijer, J. L. Hedrick, Chem. Rev. 2007, 107, 5813-5840;
16. A. Chuma, H. W. Horn, W. C. Swope, R. C. Pratt, L. Zhang, B. G. G. Lohmeijer, C. G. Wade, R. M. Waymouth, J. L. Hedrick, J. E. Rice, J. Am. Chem. Soc. 2008, 130, 6749-6754;
17. X. Sun, J. P. Gao, Z. Y. Wang, J. Am. Chem. Soc. 2008, 130, 8130-8131;
18. M. K. Kiesewetter, M. D. Scholten, N. Kirn, R. L. Weber, J. L. Hedrick, R. M. Waymouth, J. Org. Chem. 2009, 74, 9490-9496;
19. L. Zhang, R. C. Pratt, F. Nederberg, H. W. Horn, J. E. Rice, R. M. Waymouth, C. G. Wade, J. L. Hedrick, Macromolecules 2010, 43, 1660-1664.
20. N. E. Leadbeater, C. vanderPol, J. Chem. Soc. Perkin Trans. 1 2001, 2831-2835;
21. R. S. Grainger, N. E. Leadbeater, A. MasdéuPàmies, Catal. Commun. 2002, 3, 449-452;
22. V. K. Aggarwal, A. Mereu, Chem. Commun. 1999, 2311-2312.
23. C. Ghobril, C. Sabot, C. Mioskowski, R. Baati, Eur. J. Org. Chem. 2008, 4104-4108;
24. P. Hammar, C. Ghobril, C. Antheaume, A. Wagner, R. Baati, F. Himo, J. Org. Chem. 2010, 75, 4728-4736;
25. C. Ghobril, P. Hammar, S. Kodepelly, B. Spiess, A. Wagner, F. Himo, R. Baati, ChemCatChem 2010, 2, 1573-1581.
26. E. J. Corey, M. J. Grogan, Org. Lett. 1999, 1, 157-160;
27. L. Wang, X. Huang, J. Jiang, X. Liu, X. Feng, Tetrahedron Lett. 2006, 47, 1581-1584.
28. S. Kim, H. Chang, Synth. Commun. 1984, 14, 899-904;
29. T. Isobe, K. Fukuda, Y. Araki, T. Ishikawa, Chem. Commun. 2001, 243-244.
30. S. M. Ahmad, D. C. Braddock, G. Cansell, S. A. Hermitage, Tetrahedron Lett. 2007, 48, 915-918.
31. S. Huang, J. Ma, J. Li, N. Zhao, W. Wei, Y. Sun, Catal. Commun. 2008, 9, 276-280;
32. M. Costa, G. P. Chiusoli, M. Rizzardi, Chem. Commun. 1996, 1699-1700;
33. A. Barbarini, R. Maggi, A. Mazzacani, G. Mori, G. Sartori, R. Sartorio, Tetrahedron Lett. 2003, 44, 2931-2934.
34. Y. Tsuchiya, T. Kumamoto, T. Ishikawa, J. Org. Chem. 2004, 69, 8504-8505;
35. W. Disadee, T. Ishikawa, M. Kawahata, K. Yamaguchi, J. Org. Chem. 2006, 71, 6600-6603.
36. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957;
37. H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512;
38. R. Lucius, R. Loos, H. Mayr, Angew. Chem. 2002, 114, 97-102; Angew. Chem. Int. Ed. 2002, 41, 91-95;
39. H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77;
40. H. Mayr, A. R. Ofial, Pure Appl. Chem. 2005, 77, 1807-1821;
41. H. Mayr, Angew. Chem. 2011, 123, 3692-3698; Angew. Chem. Int. Ed. 2011, 50, 3612-3618;
42. For a comprehensive listing of nucleophilicity parameters N and electrophilicity parameters E, see
43. For pyridines see:
44. F. Brotzel, B. Kempf, T. Singer, H. Zipse, H. Mayr, Chem. Eur. J. 2007, 13, 336-345;
45. N. DeRycke, G. Berionni, F. Couty, H. Mayr, R. Goumont, O. R. P. David, Org. Lett. 2011, 13, 530-533; For azoles see:
46. M. Baidya, F. Brotzel, H. Mayr, Org. Biomol. Chem. 2010, 8, 1929-1935; For phosphanes see:
47. B. Kempf, H. Mayr, Chem. Eur. J. 2005, 11, 917-927; For DBU and DBN, see:
48. M. Baidya, H. Mayr, Chem. Commun. 2008, 1792-1794; For isothioureas see:
49. B. Maji, C. Joannesse, T. A. Nigst, A. D. Smith, H. Mayr, J. Org. Chem. 2011, 76, 5104-5112.
50. O. Kaumanns, H. Mayr, J. Org. Chem. 2008, 73, 2738-2745;
51. F. Seeliger, S. T. A. Berger, G. Y. Remennikov, K. Polborn, H. Mayr, J. Org. Chem. 2007, 72, 9170-9180;
52. S. T. A. Berger, F. H. Seeliger, F. Hofbauer, H. Mayr, Org. Biomol. Chem. 2007, 5, 3020-3026.
53. A crystal structure analysis revealed the constitution with NH group in the six-membered ring: F. A. Cotton, C. A. Murillo, X. Wang, C. C. Wilkinson, Inorg. Chem. 2006, 45, 5493-5500.
54. M. S. Khalaf, M. P. Coles, P. B. Hitchcock, Dalton Trans. 2008, 4288-4295.
55. 2 reported in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at
56. J. V. Greenhill, M. J. Ismail, P. N. Edwards, P. J. Taylor, J. Chem. Soc. Perkin Trans. 2 1985, 1255-1264.