Direct transformation of simple enals to 3,4-disubstituted benzaldehydes under mild reaction conditions via an organocatalytic regio- and chemoselective dimerization cascade

Chemistry - A European Journal

Volumn 18, Issue 32, 2012, Pages 9770-9774

  Song, Xixi ^a   Zhang, Xinshuai ^a   Zhang, Shilei ^a   Li, Hao ^b   Wang, Wei ^a,b  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

arenes; aromatization; cascade reactions; dimerization; organocatalysis

Indexed keywords

ARENES; CASCADE REACTIONS; CHEMO-SELECTIVITY; CHEMOSELECTIVE; DIRECT PREPARATION; MILD REACTION CONDITIONS; ORGANOCATALYSIS; ORGANOCATALYTIC;

ALDEHYDES; AROMATIZATION; REACTION KINETICS;

DIMERIZATION;

ALKENE; BENZALDEHYDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; BENZALDEHYDES; CATALYSIS; DIMERIZATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84864446955     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201709     Document Type: Article

References (33)

1. L. N. Ferguson, Chem. Rev. 1946, 38, 227
2. W. Kantlehner, Eur. J. Org. Chem. 2003, 2530
3. Modern Arene Chemistry: Concepts, Synthesis, and Applications (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2002
4. G. A. Burdock, Fenaroli's Handbook of Flavor Ingredients, 6 th ed., CRC Press, Boca Raton, 2010
5. Benzaldehyde: Webster's Timeline History, 1834-2007 (Ed.:, P. M. Parker,), ICON Group International, Inc., 2010.
6. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244
7. Angew. Chem. Int. Ed. 2003, 42, 1210
8. L. M. Salonen, M. Ellermann, F. Diederich, Angew. Chem. 2011, 123, 4908
9. Angew. Chem. Int. Ed. 2011, 50, 4808
10. L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
11. J. March, Advanced Organic Chemistry, 4 th ed., Wiley, New York, 1992, pp. 501-568
12. D. Lenoir, Angew. Chem. 2003, 115, 880
13. Angew. Chem. Int. Ed. 2003, 42, 854
14. J. Suwiński, K. Świerczek, Tetrahedron 2001, 57, 1639.
15. For a report of directed ortho metalation, see:, V. Snieckus, Chem. Rev. 1990, 90, 879.
16. A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439
17. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417
18. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
19. Angew. Chem. Int. Ed. 2009, 48, 5094.
20. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242
21. F. W. Patureau, F. Glorius, Angew. Chem. 2011, 123, 2021
22. Angew. Chem. Int. Ed. 2011, 50, 1977
23. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422
24. Angew. Chem. Int. Ed. 2011, 50, 3362.
25. X.-X. Song, A.-G. Song, F. Zhang, H.-X. Li, W. Wang, Nat. Commun. 2011, 2, 524.
26. For a Review of the applications of MacMillan's catalysts, see:, G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79.
27. For recent Reviews of diaryl prolinol catalysis, see:, A. Lattanzi, Chem. Commun. 2009, 1452.
28. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922
29. K. L. Jensen, G. Dickmeiss, H. Jiang, L. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248.
30. B. Hong, M. Wu, H. Tseng, J. Liao, Org. Lett. 2006, 8, 2217
31. B. Hong, H. Tseng, S. Chen, Tetrahedron 2007, 63, 2840.
32. Shi and co-workers observed that p-nitrophenol could facilitate the aldol process in the Morita-Baylis-Hilman reaction:, M. Shi, Y.-H. Liu, Org. Biomol. Chem. 2006, 4, 1468.
33. II- catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols:, Y. Izawa, D. Pun, S. S. Stahl, Science 2011, 333, 209.