Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex

Journal of the American Chemical Society

Volumn 130, Issue 46, 2008, Pages 15254-15255

  Takaya, Jun ^a   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CARBON DIOXIDE; CARBOXYLIC ACID; LEAD; PALLADIUM COMPLEX; SILICON;

ARTICLE; CARBOXYLATION; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON; GEOMETRY; METHYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 56449125277     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806677w     Document Type: Article

References (41)

1. 2-fixation reactions; see: (a) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
2. (b) Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27.
3. (c) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
4. (a) Johansson, R.; Wendt, O. F. Dalton Trans. 2007, 488.
5. (b) Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057.
6. (a) Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2006, 128, 8706.
7. (b) Takaya, J.; Tadami, S.; Ukai, K.; Iwasawa, N. Org. Lett. 2008, 10, 2697.
8. (c) Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 5792.
9. (a) Yeung, C. S.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 7826.
10. (b) Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 2681.
11. 2. See: (a) Takimoto, M.; Kawamura, M.; Mori, M.; Sato, Y. Synlett 2005, 2019.
12. (b) Takimoto, M.; Nakamura, Y.; Kimura, K.; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956.
13. (c) Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2002, 124, 10008.
14. 2 using terminal alkyne as substrates was reported; see: (a) Oi, S.; Fukue, Y.; Nemoto, K.; Inoue, Y. Macromolecules 1996, 29, 2694.
15. (b) Fukue, Y.; Oi, S.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1994, 2091.
16. 2 were reported although their catalytic activity, scope, yield, and product selectivity were not satisfactory; see: (a) Tsuda, T.; Yamamoto, T.; Saegusa, T. J. Organomet. Chem. 1992, 429, C46.
17. (b) Dérien, S.; Clinet, J.-C.; Duñach, E.; Périchon, J. Synlett 1990, 361.
18. (c) Sasaki, Y. J. Mol. Catal. 1989, 54, L9.
19. (d) Aresta, M.; Quaranta, E.; Ciccarese, A. C1 Mol. Chem. 1985, 1, 283.
20. (e) Döhring, A.; Jolly, P. W. Tetrahedron Lett. 1980, 21, 3021.
21. Reductive allylation of other carbonyl compounds using allene substrates were recently reported; see: (a) Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
22. (b) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134.
23. (c) Ngai, M.-Y.; Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.
24. Synthesis of several tridentate PSiP-pincer complexes have been reported although they have rarely been used as a catalyst in synthetic organic chemistry; see: (a) Gossage, R. A.; McLennan, G. D.; Stobart, S. R. Inorg. Chem. 1996, 35, 1729.
25. (b) Brost, R. D.; Bruce, G. C.; Joslin, F. L.; Stobart, S. R. Organometallics 1997, 16, 5669.
26. (c) MacInnis, M. C.; MacLean, D. F.; Lundgren, R. J.; McDonald, R.; Turculet, L. Organometallics 2007, 26, 6522. and references cited therein.
27. See also: (d) Balakrishna, M. S.; Chandrasekaran, P.; George, P. P. Coord. Chem. Rev. 2003, 241, 87.
28. (e) Minato, M.; Zhou, D.-Y.; Sumiura, K.-i.; Hirabayashi, R.; Yamaguchi, Y.; Ito, T. Chem. Commun. 2001, 2654.
29. (f) Minato, M.; Matsumoto, T.; Ichikawa, M.; Ito, T. Chem. Commun. 2003, 2968.
30. (g) Korshin, E. E.; Leitus, G.; Shimon, L. J. W.; Konstantinovski, L.; Milstein, D. Inorg. Chem. 2008, 47, 7177.
31. Allyl palladium complexes bearing PCP-pincer ligand are reported to act as nucleophilic allylation catalyst; see: Szabó, K. J. Synlett 2006, 811.
32. See ref 9 and references cited therein.
33. Oligomerization of allene was often observed as a side reaction; see ref 7e.
34. 1 was synthesized in good yield by ligand exchange of ClPd(PSiP) 2 with AgOTf. The structure of 1 was confirmed by X-ray analysis. For detailed procedure and ORTEP diagram, see Supporting Information.
35. Turculet and co-workers reported preparation of 2 during this research was in progress; see ref 9c.
36. Other solvents such as toluene, 1,4-dioxane, and THF resulted in lower conversion under the same conditions.
37. 3.
38. 3 did not afford the product.
39. 2 afforded only 9% of 3-methyl-5-phenyl-1-pentene, and 78% of 3a was recovered. Even when the same reaction was run in the presence of diethylaluminum carboxylate, nearly the same result was obtained. These results strongly suggest that the exchange of allylpalladium to allylaluminum did not occur to an appreciable amount under the present reaction conditions and carboxylation occurs mainly with the allylpalladium intermediate.
40. The stereochemistry was not determined.
41. 3 caused isomerization of the product to α,β-unsaturated carboxylic acid.