Palladium-catalyzed arylation of tert-cyclobutanols with aryl bromide via C-C bond cleavage: New approach for the γ-arylated ketones [5]

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 11010-11011

  Nishimura, Takahiro ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUTANOL; KETONE DERIVATIVE; PALLADIUM;

CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS;

EID: 0033485816     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993023q     Document Type: Letter

References (28)

1. Tsuji, J. In Palladium Reagents and Catalysis; John Wiley: New York, 1995.
2. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem.., Int. Ed. 1998, 37, 2046. Hartwig, J. F. Synlett 1997, 329. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
3. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem.., Int. Ed. 1998, 37, 2046. Hartwig, J. F. Synlett 1997, 329. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
4. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem.., Int. Ed. 1998, 37, 2046. Hartwig, J. F. Synlett 1997, 329. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
5. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem.., Int. Ed. 1998, 37, 2046. Hartwig, J. F. Synlett 1997, 329. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
6. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwig, J. F. Angew. Chem.., Int. Ed. 1998, 37, 2046. Hartwig, J. F. Synlett 1997, 329. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
7. Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 21, 2645.
8. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
9. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
10. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
11. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
12. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
13. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
14. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
15. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
16. For recent advances in palladium-catalyzed arylation of alcohols with aryl halide to produce aryl ethers, see: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333. (b) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc, 1996, 118, 13109. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395. Widenhoefer R. A.; Zhong, H, A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787. (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005. (g) Widenhoefer R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 6504. (h) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
17. For examples of C-C reductive elimination, which is much faster than β-hydrogen elimination in palladium-catalyzed arylation of ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hammann, B. C; Hartwig J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
18. For examples of C-C reductive elimination, which is much faster than β-hydrogen elimination in palladium-catalyzed arylation of ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hammann, B. C; Hartwig J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
19. For examples of C-C reductive elimination, which is much faster than β-hydrogen elimination in palladium-catalyzed arylation of ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hammann, B. C; Hartwig J. F. J. Am. Chem. Soc. 1997, 119, 12382. Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
20. For examples of C-C reductive elimination, which is much faster than β-hydrogen elimination in palladium-catalyzed arylation of ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hammann, B. C; Hartwig J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
21. Cyclobutanols are readily accessible from the corresponding cyclobutanones and Grignard reagent. For typical methods for preparing cyclobutanones, see: (a) Krepski, L. R.; Hassner, A. J. Org. Chem. 1978, 43, 2879. (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957.
22. Cyclobutanols are readily accessible from the corresponding cyclobutanones and Grignard reagent. For typical methods for preparing cyclobutanones, see: (a) Krepski, L. R.; Hassner, A. J. Org. Chem. 1978, 43, 2879. (b) Greene, A. E.; Luche, M.-J.; Serra, A. A. J. Org. Chem. 1985, 50, 3957.
23. Racemic BINAP can also be used as a ligand. For the other ligands, dppe, dppp, dppb, and dppf stand for 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, and 1,1′-bis(diphenylphosphino)ferrocene, respectively.
24. 4 (65% GLC yield of 1b).
25. The enantiomeric excess was measured by HPLC.
26. Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296.
27. 1H NMR analysis of the crude reaction mixture. It may be formed by isomerization from an initially formed β,γ-unsaturaled ketone via β-hydrogen elimination from an alkylpalladium intermediate. Similarly, from the reaction of 2a, 3-methyl-1,3-diphenyl-2-buten-1-one was isolated in 6% yield.
28. The .stereochemistry of 6b, 7b, and 8b was confirmed by the observation of the different NOE spectra (methine protons for 6b and 8b, methyl and methine protons for 7b, respectively, in these NMR spectra).