The thiolate-catalyzed intermolecular crossed tishchenko reaction: Highly chemoselective coupling of two different aromatic aldehydes

Angewandte Chemie - International Edition

Volumn 51, Issue 43, 2012, Pages 10866-10870

  Curran, Simon P ^a   Connon, Stephen J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

disproportionation; esters; hydride transfer; thiols; Tishchenko reaction

Indexed keywords

AROMATIC ALDEHYDE; CHEMOSELECTIVE COUPLING; DISPROPORTIONATIONS; HYDRIDE TRANSFERS; THIOLS; TISHCHENKO REACTION;

AROMATIC COMPOUNDS; ESTERS;

ALDEHYDES;

ALDEHYDE; BENZALDEHYDE DERIVATIVE; ESTER; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

ALDEHYDES; BENZALDEHYDES; CATALYSIS; ESTERS; SULFHYDRYL COMPOUNDS;

EID: 84867506677     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206343     Document Type: Article

References (48)

1. W. Tischtschenko, J. Russ. Phys. Chem. 1906, 38, 355
2. W. Tischtschenko, Chem. Zentralbl. 1906, 771, 1309
3. L. Claisen, Ber. Dtsch. Chem. Ges. 1887, 20, 646.
4. T. Seki, T. Nakajo, M. Onaka, Chem. Lett. 2006, 35, 824
5. O. P. Törmäkangas, A. M. P. Koskinen, Recent Res. Dev. Org. Chem. 2001, 5, 225.
6. S. Cannizzaro, Justus Liebigs. Ann. 1853, 88, 129.
7. W. C. Child, H. Adkins, J. Am. Chem. Soc. 1925, 47, 798
8. F. J. Villani, F. Nord, J. Am. Chem. Soc. 1947, 69, 2605
9. L. Lin, A. R. Day, J. Am. Chem. Soc. 1952, 74, 5133
10. T. Saegusa, T. Ueshima, J. Org. Chem. 1968, 33, 3310
11. T. Ooi, T. Miura, K. Takaya, K. Maruoka, Tetrahedron Lett. 1999, 40, 7695
12. T. Ooi, K. Ohmatsu, K. Sasaki, T. Miura, K. Maruoka, Tetrahedron Lett. 2003, 44, 3191
13. Y. Hon, C. Chang, Y. Wong, Tetrahedron Lett. 2004, 45, 3313; transition-metal-based catalysts (selected examples)
14. M. Yamashita, Y. Watanabe, T. Mitsudo, Y. Takegami, Bull. Chem. Soc. Jpn. 1976, 49, 3597
15. T. Ito, H. Horino, Y. Koshiro, A. Yamamoto, Bull. Chem. Soc. Jpn. 1982, 55, 504
16. S. H. Bergens, D. P. Fairlie, B. Bosnich, Organometallics 1990, 9, 566
17. K. Morita, Y. Nishiyama, Y. Ishii, Organometallics 1993, 12, 3748
18. M. Yamashita, T. Ohishi, Appl. Organomet. Chem. 1993, 7, 357
19. P. Barrio, M. A. Esteruelas, E. Onate, Organometallics 2004, 23, 1340
20. T. Suzuki, T. Yamada, T. Matsuo, K. Watanabe, T. Katoh, Synlett 2005, 1450
21. S. Ogoshi, Y. Hoshimoto, M. Ohashi, Chem. Commun. 2010, 46, 3354; alkali metal salts
22. M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett. 2007, 9, 2791
23. D. C. Waddell, J. Mack, Green Chem. 2009, 11, 79
24. T. Werner, J. Koch, Eur. J. Org. Chem. 2010, 6904; alkali-/earth-metal- based catalysts
25. M. R. Crimmin, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, Org. Lett. 2007, 9, 331
26. B. M. Day, N. E. Mansfield, M. P. Coles, P. B. Hitchcock, Chem. Commun. 2011, 47, 4995.
27. For the use of boric acid as a catalyst, see:, P. R. Stapp, J. Org. Chem. 1973, 38, 1433.
28. D. Ulrich, H. Jankowski, Chem. Tech. 1988, 40, 393
29. K. Weissermel, H. J. Arpe, Industrial Organic Chemistry, 4 th ed., Wiley-VCH, Weinheim, 2003
30. A. S. Hester, K. Himmler, Ind. Eng. Chem. 1959, 51, 1424.
31. J. L. Hsu, J. M. Fang, J. Org. Chem. 2001, 66, 8573
32. L. Lu, H. Y. Chang, J. M. Fang, J. Org. Chem. 1999, 64, 84.
33. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2006, 128, 4558.
34. L. Cronin, F. Manoni, C. J. O'Connor, S. J. Connon, Angew. Chem. 2010, 122, 3109
35. Angew. Chem. Int. Ed. 2010, 49, 3045
36. C. J. O'Connor, F. Manoni, S. P. Curran, S. J. Connon, New J. Chem. 2011, 35, 551.
37. S. P. Curran, S. J. Connon, Org. Lett. 2012, 14, 1074.
38. Y. Hoshimoto, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 4668.
39. For a Highlight article, see:, W. I. Dzik, L. J. Gooßen, Angew. Chem. 2011, 123, 11241
40. Angew. Chem. Int. Ed. 2011, 50, 11047.
41. Eisen had already shown that actinide-complex-catalyzed crossed Tishchenko reactions involving aromatic aldehydes of similar electronic characteristics were unselective:, T. Andrea, E. Barnea, M. S. Eisen, J. Am. Chem. Soc. 2008, 130, 2454.
42. J. M. Berg, J. L. Tymoczko, L. Stryer, Biochemistry, 5 th ed., Freeman, New York, 2002
43. A. Soukri, A. Mougin, C. Corbier, A. Wonacott, C. Branlant, G. Branlant, Biochemistry 1989, 28, 2586
44. K. D'Ambrosio, A. Pailot, F. Talfournier, C. Didierjean, E. Benedetti, A. Aubry, G. Branlant, C. Corbier, Biochemistry 2006, 45, 2978.
45. Our group in collaboration with Zeitler and co-workers employed a similar strategy to develop highly selective (mechanistically distinct) crossed acyloin reactions., S. E. O'Toole, C. A. Rose, S. Gundala, K. Zeitler, S. J. Connon, J. Org. Chem. 2011, 76, 347.
46. For example, Nicolaou et al. have employed benzyl benzoates containing o-bromo substituents (similar to 51) as key components in the total synthesis of balanol (and analogues thereof):, K. C. Nicolaou, K. Koide, M. E. Bunnage, Chem. Eur. J. 1995, 1, 454.
47. 1H NMR spectroscopy using styrene as an internal standard. The yields given for 48, 49, and 49 a are those of isolated products. For a review of the hydrogenolysis of sulfur-containing compounds using Raney nickel, see:, H. Hauptmann, W. F. Walter, Chem. Rev. 1962, 62, 347.
48. Aliphatic aldehydes containing α-unbranched aldehydes undergo preferential aldol condensation under these conditions.