Nickel-catalyzed decarbonylative addition of anhydrides to alkynes

Journal of the American Chemical Society

Volumn 130, Issue 51, 2008, Pages 17226-17227

  Kajita, Yuichi ^a   Kurahashi, Takuya ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC CYCLES; COCATALYST; ISOCOUMARINS; PHTHALIC ANHYDRIDES; REDUCTIVE ELIMINATION;

ACETYLENE; ADDITION REACTIONS; NICKEL ALLOYS;

NICKEL;

ACID ANHYDRIDE; ALKYNE; NICKEL; QUATERNARY AMMONIUM DERIVATIVE; CARBON; CHLORIDE; COUMARIN; COUMARIN DERIVATIVE; OXYGEN; PHTHALIC ANHYDRIDE; ZINC CHLORIDE; ZINC DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRICITY; HYDROGEN BOND; OLIGOMERIZATION; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; METHODOLOGY;

ALKYNES; ANHYDRIDES; CARBON; CATALYSIS; CHEMISTRY; CHLORIDES; COUMARINS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NICKEL; OXYGEN; PHTHALIC ANHYDRIDES; ZINC COMPOUNDS;

EID: 67749110110     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806569h     Document Type: Article

References (38)

1. For review of synthesis, see: (a) Barry, R. D. Chem. Rev. 1964, 64, 229.
2. (b) Jones, J. B.; Pinder. A. R. J. Chem. Soc. 1958, 2612.
3. Napolitano, E. Org. Prep. Proced. Int. 1997, 29. 631.
4. For transition metal catalyzed synthesis, see: (a) Larock. R. C.; Doty. M. J.: Han. X. J. Org. Chem. 1999 64, 8770.
5. (b) Hua, R.; Tanaka. M, New J. Chem. 2001, 25, 179.
6. Nakamura. Y.; Ukita, T. Org. Lett. 2002, 4, 2317.
7. Subramanian. V.; Batchu, V. R.; Barange, D.; Pal, M. J. Org Chem. 2005, 70, 4778.
8. (e) Cherry, K.; Parrain, J.-L.; Thibonnet. J.; Duchêne, A.; Abarbri, M. J. Org. Chem. 2005, 70, 6669.
9. (f) Kishimoto, Y.; Mitani, I. Synlett 2005, 2141.
10. (g) Fukuyama. T.; Higashibeppu. Y.; Yamaura, R.; Ryu, I. Org Lett. 2007, 9, 587.
11. (h) Luo, T.; Schreiber, S. L. Angew. Chem., Int. Ed.2007, 46, 8250.
12. Woo. J. C. S.; Walker. S. D.; Faul, M. M. Tetrahedron Lett. 2007, 48, 5679.
13. For recent examples, see: (a) Agata. N.; Nogi. Ft.; Milhollen. M.; Kharbanda, S.; Kufe. D. Cancer Res. 2004, 64. 8512.
14. (b) Pochet. L.; Frédérick, R.; Masereel, B. Curr. Pharm. Design 2004, 10. 3781.
15. Kajita, Y.: Matsubara, S.: Kurahashi, T. J. Am. Chem. Soc. 2008, 130, 6058.
16. The nickel-catalyzed addition reaction of la with 2a gaye 3aa in 72% when the reaction was carried out at elevated temperature (250 °C, 6 h, in an autoclave).
17. (a) Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779.
18. (b) Mahadevan, V.; Getzler. Y. D. Y. L.; Coates, G. W. Angew Chem., Int. Ed 2002, 41, 2781.
19. Kamijo. S.; Yamamoto, Y. Angew. Chem, Int. Ed. 2002, 41. 3230.
20. Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovskv. E. B.; Coates, G. W. J. Am Chem. Soc. 2002. 124, 1174.
21. (e) Fontaine, F.-G.; Zargarian. D. J. Am. Chem. Soc. 2004, 126, 8786.
22. (f) Ogoshi, S; Ueta. M.; Arai, T.; Kurosawa, Ft. J. Am. Chem. Soc. 2005. 127. 12810.
23. (g) Rubina, M.; Conlev, M.; Gevorgyan. V. J. Am. Chem. Soc. 2006. 128, 5818.
24. (h) Nakao, Y., Yada, A.; Ebata, S.; Hivama. T. J. Am. Chem. Soc. 2007, 129, 2428.
25. Shen. Q.; Hartwig, J. F. J. Am Chem. Soc. 2007. 129, 7734.
26. (j) Nakao, Y.; Kanviva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 2448.
27. (k) Baxter, R. D.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 9662.
28. Orglmeister, E.; Mallat, T.; Baiker, A. J. Catal. 2005, 233, 333.
29. For detailed examination of the reaction conditions, see Supporting Information Table S1.
30. 2 (20 mol %) as an additive also affords 3aa in 86% isolated yield. For detailed examination of the reaction conditions, see Supporting Information Table S2. Netherton. M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
31. While the majority of the addition reactions have been run on only a 0.5 mmol scale, a larger scale reaction (10 mmol scale) also proceeded smoothly even with reduced catalyst loading (5 mol %) without any difficulty (94% isolated yield), which illustrates the robustness of the reaction. In-situ TR spectra analysis revealed that the reaction proceeded exclusively to give the addition product and was completed in 36 h (Figure S2, Supporting Information).
32. (a) O'Brien, E. M.; Bercot. E. A.; Rovis, T. J. Am. Chem. Soc. 2003, 125, 10498.
33. (b) Johnson, J. B.; Bercot, E. A.; Rowley. J. M.; Coates, G. W.; Rovis, T. J. Am. Chem. Soc. 2007, 129. 2718.
34. (a) Trost, B. M.; Chen, F. Tetrahedron Lett. 1971, 12, 2603.
35. (b) Sano, K.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1984, 941.
36. Sano, K.; Yamamoto, T.; Yamamoto, A. Bull. chem. Soc. Jpn. 1984, 57, 2741.
37. Yamamoto. T.; Sano, K.; Yamamoto, A. J. Am. Chem. Soc. 1987, 109, 1092.
38. (e) Fischer, R.; Walther, D.; Kempe, R.; Sieler, J.; Schönecker, B. J. Qrganomet. Chem. 1993, 447, 131.