Selective 1:2 Coupling of aldehydes and allenes with control of regiochemistry

Angewandte Chemie - International Edition

Volumn 50, Issue 44, 2011, Pages 10436-10439

  Toyoshima, Takeharu ^a   Miura, Tomoya ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

aldehydes; allenes; regioselectivity; rhodium; synthetic methods

Indexed keywords

ALLENES; CATALYZED COUPLING; COUNTERIONS; IN-CONTROL; REGIOCHEMISTRY; RHODIUM COMPLEXES; SYNTHETIC METHODS;

ALDEHYDES; HYDROCARBONS; ISOMERS; KETONES; RHODIUM;

RHODIUM COMPOUNDS;

EID: 80054985558     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105077     Document Type: Article

References (29)

1. For recent reviews, see: J. Montgomery, G. J. Sormunen, Metal Catalyzed Reductive C-C Bond Formation: A Departure from Preformed Organometallic Reagents (Ed.:, M. J. Krische,), Springer, Berlin, 2007; pp. 1-23
2. R. M. Moslin, K. Miller-Moslin, T. F. Jamison, Chem. Commun. 2007, 4441
3. J. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische, Angew. Chem. 2009, 121, 36
4. Angew. Chem. Int. Ed. 2009, 48, 34
5. M. C. Willis, Chem. Rev. 2010, 110, 725.
6. S.-S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 7320
7. S.-S. Ng, T. F. Jamison, Tetrahedron 2006, 62, 11350.
8. M. Song, J. Montgomery, Tetrahedron 2005, 61, 11440.
9. For examples of the preparation of homoallylic alcohols by reactions of aldehydes, allenes, and organoboron or organozinc compounds catalyzed by palladium(II) and rhodium(I) complexes, see: C. D. Hopkins, H. C. Malinakova, Org. Lett. 2004, 6, 2221
10. C. D. Hopkins, L. Guan, H. C. Malinakova, J. Org. Chem. 2005, 70, 6848
11. T. Bai, S. Ma, G. Jia, Tetrahedron 2007, 63, 6210
12. Y. Yoshida, K. Murakami, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2010, 132, 8878.
13. E. Skucas, J. F. Bower, M. J. Krische, J. Am. Chem. Soc. 2007, 129, 12678
14. J. F. Bower, E. Skucas, R. L. Patman, M. J. Krische, J. Am. Chem. Soc. 2007, 129, 15134
15. S. B. Han, I. S. Kim, H. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 6916
16. E. Skucas, J. R. Zbieg, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 5054.
17. J. D. Osborne, H. E. Randell-Sly, G. S. Currie, A. R. Cowley, M. C. Willis, J. Am. Chem. Soc. 2008, 130, 17232
18. H. E. Randell-Sly, J. D. Osborne, R. L. Woodward, G. S. Currie, M. C. Willis, Tetrahedron 2009, 65, 5110.
19. For a similar allene hydroacylation reaction using salicylaldehyde, see:, K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1999, 72, 303.
20. T. Miura, T. Biyajima, T. Toyoshima, M. Murakami, Beilstein J. Org. Chem. 2011, 7, 578.
21. For palladium-catalyzed 1:2 coupling reactions of nucleophiles (e.g. carboxylic acids, amines, and water) and allenes, see: G. D. Shier, J. Organomet. Chem. 1967, 10, P 15
22. D. R. Coulson, J. Org. Chem. 1973, 38, 1483
23. Y. Inoue, Y. Ohtsuka, H. Hashimoto, Bull. Chem. Soc. Jpn. 1984, 57, 3345
24. C. H. Oh, H. S. Yoo, S. H. Jung, Chem. Lett. 2001, 1288.
25. For rhodium-catalyzed reductive 1:2 coupling reactions of aldehydes and acetylenes, see: J. R. Kong, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16040
26. V. M. Williams, J. R. Kong, B. J. Ko, Y. Mantri, J. S. Brodbelt, M.-H. Baik, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 16054.
27. For the effect of halide ions on regioselectivity in a rhodium-catalyzed allylic substitution reaction, see:, P. A. Evans, D. K. Leahy, L. M. Slieker, Tetrahedron: Asymmetry 2003, 14, 3613.
28. Another mechanism involving oxidative cyclization of a homopair of allenes followed by the insertion of an aldehyde is also conceivable. For examples of isolated rhodacyclopentanes prepared from two molecules of an allene, see: G. Ingrosso, L. Porri, G. Pantini, P. Racanelli, J. Organomet. Chem. 1975, 84, 75
29. J.-C. Choi, S. Sarai, T. Koizumi, K. Osakada, T. Yamamoto, Organometallics 1998, 17, 2037.