Beyond Aresta's complex: Ni- and Pd-catalyzed organozinc coupling with CO2

Journal of the American Chemical Society

Volumn 130, Issue 25, 2008, Pages 7826-7827

  Yeung, Charles S ^a   Dong, Vy M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; METAL COMPLEX; NICKEL; PALLADIUM; ZINC DERIVATIVE;

ARTICLE; CARBOXYLATION; CATALYSIS; CROSS COUPLING REACTION; CYCLOADDITION; ELIMINATION REACTION; REDUCTION;

EID: 45749157241     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803435w     Document Type: Article

References (35)

1. Recent reviews: (a) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
2. (b) Louie, J. Curr. Org. Chem. 2005, 9, 605.
3. (c) Aresta, M.; Dibenedotto, A. Dalton Trans. 2007, 2975.
4. Carboxylation of organocuprates: (a) Ebert, G. W.; Juda, W. L.; Kosakowski, R. H.; Ma, B.; Dong, L.; Cummings, K. E.; Phelps, M. V. B.; Mostafa, A. E.; Luo, J. J. Org. Chem. 2005, 70, 4314.
5. (b) Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2006, 128, 8706.
6. Review of organozinc reagents: Knochel, P.; Calaza, M. I.; Hupe, E. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinhelm, Germany, 2004; Vol. 1, Chapter 11.
7. Carbonylation of C-X bonds is a complimentary strategy: Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons, Inc.: New York, 2002; Part VI.
8. (a) Aresta, M.; Nobile, C. F.; Albano, V. G.; Forni, E.; Manassero, M. J. Chem. Soc., Chem. Commun. 1975, 15, 636.
9. Spectroscopic investigations: (b) Aresta, M.; Nobile, C. F. J. Chem. Soc., Dalton Trans. 1977, 708.
10. Stoichiometric reactions: (c) Aresta, M.; Gobetto, R.; Quaranta, E.; Tommasi, I. Inorg. Chem. 1992, 31, 4286.
11. (d) Tommasi, I.; Aresta, M.; Giannoccaro, P.; Quaranta, E.; Fragale, C. Inorg. Chim. Acta 1998, 272, 38.
12. (e) Wright, C. A.; Thorn, M.; McGill, J. W.; Sutterer, A.; Hinze, S. M.; Prince, R. B.; Gong, J. K. J. Am. Chem. Soc. 1996, 118, 10305.
13. Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27.
14. Other Ni(0)-catalyzed carboxylations: (a) Takimoto, M.; Nakamura, Y.; Kimura, K.; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956.
15. (b) Tekavec, T. N.; Arif, A. M.; Louie, J. Tetrahedron 2004, 60, 7431.
16. Transmetalation in analogous six-membered nickelocycles has been reported: Bercot, E.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 247.
17. (a) Olah, G. A.; Török, B.; Joshek, J. P.; Busci, I.; Esteves, P. M.; Rasul, G.; Prakash, G. K. S. J. Am. Chem. Soc. 2002, 124, 11379.
18. (b) Nemoto, K.; Yoshida, H.; Suzuki, Y.; Morohashi, N.; Hattori, T. Chem. Lett. 2006, 35, 820.
19. 2) intermediate in catalysis have been reported: (a) Dérien, S.; Clinet, J.-C.; Duñach, E.; Périchon, J. J. Org. Chem. 1993, 58, 2578.
20. (b) Walther, D.; Schönberg, H.; Dinjus, E.; Sieler, J. J. Organomet. Chem. 1987, 334, 377.
21. (a) Jolly, P. W.; Jonas, K.; Kruger, C.; Tsay, Y.-H. J. Organomet. Chem. 1971, 33, 109.
22. (b) Darensbourg, M. H.; Ludwig, M.; Riordan, C. G. Inorg. Chem. 1989, 28, 1630.
23. 2 could not be observed spectroscopically.
24. Homocoupling is one possibility for reduction: (a) Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem. - Eur. J. 2006, 12, 4749.
25. (b) Wang, J.-X.; Wang, K.; Zhao, L.; Li, H.; Fu, Y.; Hu, Y. Adv. Synth. Catal. 2006, 348, 1262.
26. See Supporting Information for details.
27. (a) Fillon, H.; Gosmini, C.; Périchon, J. J. Am. Chem. Soc. 2003, 125, 3867.
28. Arylzinc reagents can also be prepared by (i) insertion of highly active zinc to C-Br bonds: (b) Rieke, R. D. Aldrichimica Acta 2000, 33, 52
29. or (ii) transmetalation: (c) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
30. (d) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
31. 2 was not a suitable precatalyst. See Supporting Information.
32. 2 in alkylzinc carboxylation resulted in lower yields.
33. Alkylzinc reagent preparation: Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 43, 6040.
34. Carboxylation of allylstannanes is known but is subject to significant scrambling: (a) Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057.
35. (b) Johansson, R.; Wendt, O. F. Dalton Trans. 2007, 488.