Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2315-2318

  Gelman, Dmitri ^a   Jiang, Lei ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIAMINE DERIVATIVE; N,N' DIMETHYLETHYLENEDIAMINE; PHOSPHINE DERIVATIVE; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; STEREOCHEMISTRY;

CATALYSIS; COPPER; HYDROCARBONS, AROMATIC; HYDROCARBONS, HALOGENATED; PHOSPHINES; PHOSPHITES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0141741556     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0346640     Document Type: Article

References (41)

1. For reviews, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
2. For reviews, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
3. For example: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
4. For example: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
5. For example: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
6. For example: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
7. For example: (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529. (e) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
8. (a) Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202.
9. (b) Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
10. (c) Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718.
11. (d) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
12. (e) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
13. For a review, see: (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. For copper-catalyzed C-S bond formation, see: (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
14. For a review, see: (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. For copper-catalyzed C-S bond formation, see: (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
15. For a review, see: (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. For copper-catalyzed C-S bond formation, see: (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
16. (a) Brauer, D. J.; Hingst, M.; Kottsieper, K. W.; Liek, C.; Nickel, T.; Tepper, M.; Stelzer, O.; Sheldrick, W. S. J. Organomet. Chem. 2002, 645, 14.
17. (b) Stadler, A.; Kappe, C. O. Org. Lett. 2002, 4, 3541.
18. (c) Kraatz, H.-B.; Pletsch, A. Tetrahedron: Asymmetry 2000, 11, 1617.
19. (d) Bergbreiter, D. E.; Liu, Y.-S.; Furyk, S.; Case, B. L. Tetrahedron Lett. 1998, 39, 8799.
20. (e) Machnitzki, P.; Nickel, T.; Stelzer, O.; Landgrafe, C. Eur. J. Inorg. Chem. 1998, 1029.
21. (f) Herd, O.; Hessler, A.; Hingst, M.; Trepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
22. (g) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
23. Selected recent publications: (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583. After this manuscript was submitted, a paper describing the Cu-catalyzed coupling of diphenylphosphine and aryl iodides appeared on the web: (e) Van Allen, D.; Venkataraman, D. J. Org. Chem. Published ASAP May 2, 2003.
24. Selected recent publications: (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583. After this manuscript was submitted, a paper describing the Cu-catalyzed coupling of diphenylphosphine and aryl iodides appeared on the web: (e) Van Allen, D.; Venkataraman, D. J. Org. Chem. Published ASAP May 2, 2003.
25. Selected recent publications: (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583. After this manuscript was submitted, a paper describing the Cu-catalyzed coupling of diphenylphosphine and aryl iodides appeared on the web: (e) Van Allen, D.; Venkataraman, D. J. Org. Chem. Published ASAP May 2, 2003.
26. Selected recent publications: (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583. After this manuscript was submitted, a paper describing the Cu-catalyzed coupling of diphenylphosphine and aryl iodides appeared on the web: (e) Van Allen, D.; Venkataraman, D. J. Org. Chem. Published ASAP May 2, 2003.
27. Selected recent publications: (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583. After this manuscript was submitted, a paper describing the Cu-catalyzed coupling of diphenylphosphine and aryl iodides appeared on the web: (e) Van Allen, D.; Venkataraman, D. J. Org. Chem. Published ASAP May 2, 2003.
28. Ogawa, T.; Usuki, N.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1998, 2953.
29. (a) Raboisson, P.; Baurand, A.; Cazenave, J.-P.; Gachet, C.; Schultz, D. ; Spiess, B.; Bourguigon, J.-J. J. Org. Chem. 2002, 67, 8063.
30. (b) Holstein, S. A.; Cermak, D. M.; Wiemer, D. F.; Lewis, K.; Hohl, R. J. Bioorg. Med. Chem. 1998, 6, 687.
31. (c) Lazrek, H. B.; Rochdi, A.; Khaider, H.; Barascut, J. L.; Imbach, J. L.; Balzarini, J.; Witvrouw, M.; Pannecouque, C.; De Clercq, E. Tetrahedron 1998, 54, 3807.
32. (d) Smith, P. W.; Chamiec, A. J.; Cobley, K. N.; Duncan, K.; Howes, P. D.; Whittington, A. R.; Wood, M. R. J. Antibiot. Tokyo 1995, 48, 73.
33. Welch, C. M.; Gonzales, E. J.; Guthrie, J. D. J. Org. Chem. 1961, 26, 3270.
34. Jin, J. I. U.S. Patent 74-496233; Chem. Abstr. 1979, 90, 153010m.
35. Up to 70% of conversion to the reduced products were found in all reactions using ortho-substituted aryl iodides.
36. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
37. Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334.
38. (a) Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 729.
39. (b) Quntar, A. A. A.; Srebnik, M. Org. Lett. 2001, 3, 1379.
40. (c) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595.
41. Urch, C. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. S., Metz-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, New York, 1995; Vol. 2, Chapter 2.16, pp 622-625 and 628-630