Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a Grignard reagent with an alkyl sulfonate

Journal of the American Chemical Society

Volumn 119, Issue 9, 1997, Pages 2125-2133

  Burns, Dennis H ^a   Miller, Jeffrey D ^a   Chan, Ho Kit ^a   Delaney, Michael O ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030964143     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963944q     Document Type: Article

References (27)

1. The term "higher order" cuprates, as used in this paper, is meant to imply only a stoichiometric relationship within the cuprate. For recent information on the structure of "higher order" cuprates, see: (a) Stemmler, T. L.; Barnhart, T. M.; Penner-Hahn, J. E.; Tucker, C. E.; Knochel, P.; Böhme, M.; Frenking, G. J. Am. Chem. Soc. 1995, 117, 12489-12497. (b) Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312-4313. (c) Barnhart, T. M.; Huang, H.; Penner-Hahn, J. E. J. Org. Chem. 1995, 60, 4310-4311. (d) Snyder, J. P.; Spangler, D. P.; Behling, J. R. J. Org. Chem. 1995, 59, 2665-2667.
2. The term "higher order" cuprates, as used in this paper, is meant to imply only a stoichiometric relationship within the cuprate. For recent information on the structure of "higher order" cuprates, see: (a) Stemmler, T. L.; Barnhart, T. M.; Penner-Hahn, J. E.; Tucker, C. E.; Knochel, P.; Böhme, M.; Frenking, G. J. Am. Chem. Soc. 1995, 117, 12489-12497. (b) Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312-4313. (c) Barnhart, T. M.; Huang, H.; Penner-Hahn, J. E. J. Org. Chem. 1995, 60, 4310-4311. (d) Snyder, J. P.; Spangler, D. P.; Behling, J. R. J. Org. Chem. 1995, 59, 2665-2667.
3. The term "higher order" cuprates, as used in this paper, is meant to imply only a stoichiometric relationship within the cuprate. For recent information on the structure of "higher order" cuprates, see: (a) Stemmler, T. L.; Barnhart, T. M.; Penner-Hahn, J. E.; Tucker, C. E.; Knochel, P.; Böhme, M.; Frenking, G. J. Am. Chem. Soc. 1995, 117, 12489-12497. (b) Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312-4313. (c) Barnhart, T. M.; Huang, H.; Penner-Hahn, J. E. J. Org. Chem. 1995, 60, 4310-4311. (d) Snyder, J. P.; Spangler, D. P.; Behling, J. R. J. Org. Chem. 1995, 59, 2665-2667.
4. The term "higher order" cuprates, as used in this paper, is meant to imply only a stoichiometric relationship within the cuprate. For recent information on the structure of "higher order" cuprates, see: (a) Stemmler, T. L.; Barnhart, T. M.; Penner-Hahn, J. E.; Tucker, C. E.; Knochel, P.; Böhme, M.; Frenking, G. J. Am. Chem. Soc. 1995, 117, 12489-12497. (b) Snyder, J. P.; Bertz, S. H. J. Org. Chem. 1995, 60, 4312-4313. (c) Barnhart, T. M.; Huang, H.; Penner-Hahn, J. E. J. Org. Chem. 1995, 60, 4310-4311. (d) Snyder, J. P.; Spangler, D. P.; Behling, J. R. J. Org. Chem. 1995, 59, 2665-2667.
5. For reviews on the substitution chemistry of cuprates, see: (a) Lipshutz, B. H. Org. React. (N. Y.) 1992, 41, 135-631. (b) Lipshutz, B. H.; Wihelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. (c) Posner, G. H. Org. React. (N. Y.) 1975, 22, 253-400.
6. For reviews on the substitution chemistry of cuprates, see: (a) Lipshutz, B. H. Org. React. (N. Y.) 1992, 41, 135-631. (b) Lipshutz, B. H.; Wihelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. (c) Posner, G. H. Org. React. (N. Y.) 1975, 22, 253-400.
7. For reviews on the substitution chemistry of cuprates, see: (a) Lipshutz, B. H. Org. React. (N. Y.) 1992, 41, 135-631. (b) Lipshutz, B. H.; Wihelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005-5038. (c) Posner, G. H. Org. React. (N. Y.) 1975, 22, 253-400.
8. (a) Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777-7782. Following the submission of this manuscript, a communication appeared that demonstrated the efficient transfer of a butyl group to benzoyl chloride and 2-cyclohexenone from mixed β-silyl cuprates: Bertz, S. H.; Eriksson, M.; Miao, G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 10906-10907.
9. (a) Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7777-7782. Following the submission of this manuscript, a communication appeared that demonstrated the efficient transfer of a butyl group to benzoyl chloride and 2-cyclohexenone from mixed β-silyl cuprates: Bertz, S. H.; Eriksson, M.; Miao, G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 10906-10907.
10. (a) Tamura, M.; Kochi, J. K. J. Organomet. Chem. 1972, 14, 205-228.
11. (b) Posner, G. H.; Whitten, C. E.; Sterling, J. J. J. Am. Chem. Soc. 1973, 95, 7788-7800 and references contained therein.
12. Burns, D. H.; Miller, J. D. Tetrahedron Lett. 1994, 35, 5189-5192
13. Burns, D. H.; Miller, J. D.; Santana, J. J. Org. Chem. 1993, 58, 6526-6528.
14. Drouin, J.; Leyendecker, F.; Conia, J. M. Tetrahedron 1980, 36, 1195-1201.
15. Kadkhodayan, M.; Singleton, T.; Heldrich, F. O. Synth. Commun. 1984, 14, 707-712.
16. Wuping, M.; Wilcoxen, K. M.; Szewczyk, J. W.; Ibers, J. A. J. Org. Chem. 1995, 60, 8081-8083.
17. Zhang, H.-Y.; Blaskó, A.; Yu, J.-Q.; Bruice, T. C. J. Am. Chem. Soc. 1992, 114, 6621-6630.
18. Fouquet, G.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1974, 13, 82-83.
19. Hathaway, B. J. Copper. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: New York, 1987; Vol. 5, pp 536-538.
20. Tamura, M.; Kochi, J. Synthesis 1971, 303-305.
21. Wurtz dimers refers to homocoupled Grignard reactants. In this Paper, the yields and identities of the Wurtz byproducts eicosane, 1,6-diphenylhexane, and biphenyl were determined from authenticated samples and GC/MS.
22. Bajgrowicz, J. A.; Hallaoui, A. E.; Jacquier, R.; Pigiere, C.; Viallefont, P. Tetrahedron 1985, 41, 1833-1843.
23. Nunomoto, S.; Kawakami, Y.; Yamashita, Y. J. Org. Chem. 1983, 48, 1912-1914.
24. Normant, J. F.; Villieras, J.; Scott, F. Tetrahedron Lett. 1977, 3263-3266.
25. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390-2392.
26. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797.
27. Huang, H.; Alvarez, K.; Qiang, L.; Barnhart, T. M.; Snyder, J. P.; Penner-Hahn, J. E. J. Am. Chem. Soc. 1996, 118 8808-8816.