One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the sonogashira coupling reaction

Organic Letters

Volumn 4, Issue 19, 2002, Pages 3199-3202

  Mio, Matthew J ^a   Kopel, Lucas C ^a   Braun, Julia B ^a   Gadzikwa, Tendai L ^a   Hull, Kami L ^a   Brisbois, Ronald G ^a   Markworth, Christopher J ^b   Grieco, Paul A ^b  

^a MACALESTER COLLEGE   (United States)

^b MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FUSED HETEROCYCLIC RINGS; PALLADIUM; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; SYNTHESIS; TEMPERATURE;

CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS, 2-RING; LIGHT; MOLECULAR STRUCTURE; PALLADIUM; SOLVENTS; TEMPERATURE;

EID: 0037136485     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026266n     Document Type: Article

References (31)

1. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
2. Moore, J. S. Acc. Chem. Res. 1997, 30, 402.
3. Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
4. (a) Pugh, V. J.; Hu, Q.-S.; Zuo, X.; Lewis, F. D.; Pu, L. J. Org. Chem. 2001, 66, 6136.
5. (b) Hu, Q.-S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528.
6. Wan, W. B.; Haley, M. M. J. Org. Chem. 2001, 66, 3893.
7. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
8. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
9. (a) Eaborn, C.; Walton, D. R. M. J. Organomet. Chem. 1965, 4, 217.
10. (b) Eastmond, R.; Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 4601.
11. (c) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10.
12. (a) Denmark, S. E.; Sweis, R. J. Am. Chem. Soc. 2001, 123, 6439.
13. (b) Pugh, C.; Percec, V. J. Polym. Sci., Part A: Polym. Chem. 1990, 28, 1101.
14. (c) Chow, H.-F.; Wan, C-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910.
15. (d) Shultz, D. A.; Gwaltney, K. P.; Lee, H. J. Org. Chem. 1998, 63, 4034.
16. (e) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020.
17. While several procedures for generating bisarylethynylenes using alkynylmetal reagents are known, we only compare our method to similar Pd- and Cu-based strategies. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions: Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 5.
18. (b) Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1995.
19. Johannessen, S. C.; Brisbois, R. G.; Fischer, J. P.; Grieco, P. A.; Counterman, A. E.; Clemmer, D. E. J. Am. Chem. Soc. 2001, 123, 3818.
20. Use of DBU in Sonogashira-type couplings has been previously reported: Bodwell, G. J.; Miller, D. O.; Vermeij, R. J. Org. Lett. 2001, 3, 2093.
21. We ascribe this observation to the known comparison of the reaction rates of DBU (faster) and DBN (slower) in elimination reactions. Encyclopedia of Reagents for Organic Synthesis; Raquette, L. A., Ed.; John Wiley & Sons: New York, 1995.
22. (a) Correia, R.; DeShong, P. J. Org. Chem. 2001, 66, 7159.
23. (b) Manoso, A. S.; DeShong, P. J. Org. Chem. 2001, 66, 7449 and references therein.
24. 2 and 10 mol % CuI.
25. Grieco, P. A.; Markworth, C. J. Tetrahedron Lett. 1999, 40, 665.
26. a of 24. Kalijurand, I.; Rodima, T.; Leito, I.; Koppel, I. A.; Schwesinger, R. J. Org. Chem. 2000, 65, 6202.
27. a of 24. Kalijurand, I.; Rodima, T.; Leito, I.; Koppel, I. A.; Schwesinger, R. J. Org. Chem. 2000, 65, 6202.
28. Jiang, N.; Wang, J. Tetrahedron Lett. 2002, 43, 1285.
29. Li, C.-J.; Chen, D.-L.; Costello, C. W. Org. Process Res. Dev. 1997, 1, 325.
30. 4-Bromobenzonitrile gave only a trace (< 1%) of the bisarylethyne product, and complete recovery of starting material was observed for 4-bromo-N,N-dimethylaniline and 4-bromobiphenyl. Other unsuccessful attempts suggest that a detrimental single-electron-transfer pathway may take precedence over cross-coupling in certain substrates. Two iodides we investigated (1-iodo-4-nitrobenzene and 1-iodo-3,5-dinitrobenzene) and two bromides (4-bromobenzophenone and 5-bromopyrimidine) gave no discernible products when subjected to our reaction conditions.
31. Huang, S.; Tour, J. M. J. Am. Chem. Soc. 1999, 121, 4908.