Room Temperature Catalytic Animation of Aryl Iodides

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6066-6068

  Wolfe, John P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001374741     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970876x     Document Type: Article

References (28)

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2. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
3. (c) An example of an intramolecular carbon-nitrogen bond forming process which proceeds at room temperature has been reported: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
4. (d) Wolfe, J. P.; Wagaw. S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 228, 7215-7216.
5. (e) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
6. (f) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
7. (g) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
8. (h) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 62, 1133-1135.
9. (i) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267.
10. (j) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273.
11. (k) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568-1569.
12. Jeffery has reported that Heck arylations may be run at lower temperatures in the presence of stoichiometric amounts of tetraalkylammonium salts. We found that these reagents were not effective promoters of the aryl amination process at room temperature. (a) Jeffery, T. Tetrahedron 1996, 52, 10113-10130.
13. Suzuki reactions which proceed at room temperature in the presence of TlOH have also been reported. (b) Uenishi, J.-I.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758. (c) Anderson, J. C.; Namli, H. Synlett 1995, 765-766.
14. Suzuki reactions which proceed at room temperature in the presence of TlOH have also been reported. (b) Uenishi, J.-I.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758. (c) Anderson, J. C.; Namli, H. Synlett 1995, 765-766.
15. Widenhoefer, R. A.; Buchwald, S. L. Unpublished results.
16. Use of 18-crown-6 to promote one example of the Ullmann aryl ether synthesis (at 150 °C) has been reported. Jung, M. E.; Jachiet, D.; Rohloff, J. C. Tetrahedron Lett. 1989, 30, 4211-4214.
17. 1h afforded this product in only 59% isolated yield (Table 2, entry 9). The reaction of N,N-diethyl-4-iodobenzamide with n-hexylamine also gave a higher yield when the room temperature conditions were employed (Table 2, entry 1).
18. It is interesting to note that the reaction of 4-bromoiodobenzene with piperidine only proceeded to 79% conversion in THF at 65 °C in the absence of 18-C-6 (1 mol % Pd catalyst). This coupling went to completion and afforded the product in high yield (Table 2, entry 8) when the room temperature/18-C-6 conditions were employed.
19. (S)-BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl; (R)-Tol-BINAP = 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl. Racemic BINAP is now commercially available from Strem Chemical Company.
20. DPPF = 1,1′-bis(diphenylphosphino)ferrocene.
21. 3/BINAP. Wolfe, J. P.; Marcoux, J. F.; Buchwald, S. L. Unpublished results. For a successful method for the coupling of these amines, see ref 1k.
22. Verardo, G.; Giumanini, A. G.; Favret, G.; Strazzolini, P. Synthesis 1991, 447-450.
23. Dictionary of Organic Compounds, 6th ed.; Cazoga, J. I. G., Ley, S. V., Pattenden, G., Raphael, R. A., Rees, C. W., Eds; Chapman & Hall; London, 1996.
24. Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058.
25. Shim, S. C., Huh, K. T.; Park, W. H. Tetrahedron 1986, 42, 259-263.
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