An oxidative carbon-carbon bond-forming reaction proceeds via an isolable iminiumion

Pure and Applied Chemistry

Volumn 83, Issue 3, 2011, Pages 655-665

  Tsang, Althea S K ^a   Jensen, Paul ^a   Hook, James M ^b   Hashmi, A Stephen K ^c   Todd, Matthew H ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

C C bond formation; DDQ; Iminium ion; Mechanism; Oxidative coupling

Indexed keywords

BOND-FORMING REACTIONS; C-C BOND FORMATION; CARBON-CARBON BOND-FORMING REACTIONS; DDQ; DEHYDROGENATIVE COUPLING; ELEMENTAL ANALYSIS; IMINIUM; IMINIUM ION; MALONATES; ONE-POT REACTION; OXIDATIVE COUPLINGS; SOLID-STATE NMR SPECTROSCOPY;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

IONS;

EID: 79951818730     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-11-01-01     Document Type: Article

References (35)

1. C. J. Li. Acc. Chem. Res. 42, 335 (2009).
2. (a) C. J. Scheuermann. Chem. Asian J. 5, 436 (2010); for electrochemical methods of achieving similar transformations, see
3. (b) J. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki. Chem. Rev. 108, 2265 (2008).
4. Z. P. Li, C. J. Li. Eur. J. Org. Chem. 3173 (2005).
5. Y. Hayashi, T. Mukaiyama. Chem. Lett. 1811 (1987).
6. Y.-C. Xu, C. Roy, E. Lebeau. Tetrahedron Lett. 34, 8189 (1993).
7. B.-P. Ying, B. G. Trogden, D. T. Kohlman, S. X. Liang, Y.-C. Xu. Org. Lett. 6, 1523 (2004).
8. Y. Zhang, C.-J. Li. J. Am. Chem. Soc. 128, 4242 (2006).
9. W. Tu, L. Liu, P. E. Floreancig. Angew. Chem., Int. Ed. 47, 4184 (2008).
10. C. Dubs, Y. Hamashima, N. Sasamoto, T. M. Seidel, S. Suzuki, D. Hashizume, M. Sodeoka. J. Org. Chem. 73, 5859 (2008).
11. D. Cheng, W. Bao. Adv. Synth. Catal. 350, 1263 (2008).
12. L. Liu, P. E. Floreancig. Org. Lett. 11, 3152 (2009).
13. C. Guo, J. Song, S.-W. Luo, L.-Z. Gong. Angew. Chem., Int. Ed. 49, 5558 (2010).
14. L. Zhai, R. Shukla, R. Rathore. Org. Lett. 11, 3474 (2009).
15. L. Liu, P. E. Floreancig. Org. Lett. 12, 4686 (2010).
16. A. S.-K. Tsang, M. H. Todd. Tetrahedron Lett. 50, 1199 (2009).
17. O. Basĺ, C.-J. Li. Green Chem. 8, 1047 (2007).
18. Z. Li, D. S. Bohĺ, C.-J. Li. Proc. Natl. Acad. Sci. USA 103, 8928 (2006).
19. A. Guy, A. Lemor, D. Imbert, M. Lemaire. Tetrahedron Lett. 30, 327 (1989).
20. J. A. Steenkamp, C. H. L. Mouton, D. Ferreira. Tetrahedron 47, 6705 (1991).
21. H. H. Jung, P. E. Floreancig. Tetrahedron 65, 10830 (2009).
22. A. Sud, D. Sureshkumar, M. Klussmann. Chem. Commun. 3169 (2009).
23. F. Benfatti, M. G. Capdevila, L. Zoli, E. Benedetto, P. G. Cozzi. Chem. Commun. 5919 (2009).
24. X.-H. Ho, S.-I. Mho, H. Kang, H.-Y. Jang. Eur. J. Org. Chem. 4436 (2010).
25. For an example of solid formation in other DDQ-based reactions (where the identity of the solid is not unambiguously established), see: B. Bortolotti, R. Leardini, D. Nanni, G. Zanardi. Tetrahedron 49, 10157 (1993).
26. K. M. Zaman, S. Yamamoto, N. Nishimura, J. Maruta, S. Fukuzumi. J. Am. Chem. Soc. 116, 12099 (1994).
27. S. Yamamoto, T. Sakurai, L. Yingjin, Y. Sueishi. Phys. Chem. Chem. Phys. 1, 833 (1999).
28. S. V. Rosokha, D. Sun, J. Fisher, J. K. Kochi. ChemPhysChem 9, 2406 (2008).
29. H. D. Becker, B. W. Skelton, A. H. White. Aust. J. Chem. 40, 625 (1987).
30. R. Foster. Organic Charge-Transfer Complexes, 1st ed., Chap. 6, Academic Press (1969).
31. D. Sun, S. V. Rosokha, J. K. Kochi. J. Phys. Chem. B 111, 6655 (2007).
32. W. M. Haynes (Ed.). CRC Handook of Chemistry and Physics, 91st ed., CRC Press, Boca Raton (2010).
33. V. Ganesan, S. V. Rosokha, J. K. Kochi. J. Am. Chem. Soc. 125, 2559 (2003).
34. Z. Li, C.-J. Li. J. Am. Chem. Soc. 127, 6968 (2005).
35. Y. Shen, M. Li, S. Wang, T. Zhan, Z. Tan, C.-C. Guo. Chem. Commun. 953 (2009).