Photostimulated reactions of phenylacetic acid dianions with aryl halides. Influence of the metallic cation on the regiochemistry of arylation

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2643-2646

  Nwokogu, Godson C ^a,b   Wong, Jim Wah ^a   Greenwood, Thomas D ^a   Wolfe, James F ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b HAMPTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; PHENYLACETIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; RADIATION EXPOSURE; ULTRAVIOLET RADIATION;

CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; METALS; PHENYLACETATES; PHOTOCHEMISTRY; ULTRAVIOLET RAYS;

EID: 0034710463     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006177f     Document Type: Article

References (26)

1. Wong, J.-W.; Natalie, K. J.; Nwokogu, G. C.; Pisipati, J. S.; Flaherty, P. T.; Greenwood, T. D.; Wolfe, J. F. J. Org. Chem. 1997, 62, 6152-6159.
2. Wong, J.-W. Ph.D. Dissertation, Virginia Polytechnic Institute and State University, 1981.
3. Hermann, C. K. F.; Sachdeva, Y. P.; Wolfe, J. F. J. Heterocycl. Chem. 1984, 24, 1061-1065.
4. Hermann, C. K. F. Ph.D. Dissertation, Virginia Polytechnic Institute and State University, 1984.
5. Bunnett, J. F.; Gloor, B. F. J. Org. Chem. 1973, 38, 4156-4163.
6. RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983.
7. (b) Norris, R. K. Compr. Org. Synth. 1991, 4, 451-482.
8. (c) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. Org. React. 1999, 54, 1-271.
9. RN1 mechanisms; see: Tolbert, L. M.; Martone, D. P. J. Org. Chem. 1983, 48, 1185-1190.
10. RN1 reactions involving ortho and para coupling of nitranions derived from aromatic amines, see: Kim, J. K.; Bunnett, J. F. J. Am. Chem. Soc. 1970, 92, 7464-7466.
11. (b) Pierini, A. B.; Baumgartner, M. T.; Rossi, R. A. Tetrahedron Lett. 1987, 28, 4653-4656.
12. RN1 mechanism have been reported; see: Rossi, R. A.; Pierini, A. B.; Santiago, A. N. Org. React. 1999, 54, 137-157.
13. Renaud, P.; Fox, M. A. J. Org. Chem. 1988, 53, 3745-3752.
14. Lambert, J. B.; Wharry, S. M. J. Am. Chem. Soc. 1982, 104, 5857-5862.
15. 1H NMR spectrum of reaction mixtures precluded arylation at the α-carbon of 1c.
16. (a) Hauser, C. R.; Chambers, W. J. J. Am. Chem. Soc. 1956, 78, 4942-4944.
17. (b) Meyer, R. B.; Hauser, C. R. J. Org. Chem. 1961, 26, 3296-3698.
18. Shorter reaction times resulted in lower product yields, e.g., after a 2 h reaction period only 22% of 5d was obtained.
19. 4), and concentrated to a pale yellow oil that solidified on standing; 2.47 g of essentially pure phenylacetic acid. Evaporation of the hexane solution under vacuum left 0.15 g of 4-bromoanisole.
20. (a) Hoffman, A. K.; Feldman, A. M.; Geblum, E.; Hodgson, W. G. J. Am. Chem. Soc. 1964, 86, 639-646.
21. (b) Nelsen, S. F.; Bartlett, P. D. J. Am. Chem. Soc. 1966, 88, 143-149.
22. (c) Carver, D. R.; Hubbard, J. S.; Wolfe, J. F. J. Org. Chem. 1982, 47, 1036-1040.
23. By comparison, monoanion 1a reacts with iodobenzene under essentially identical conditions to give 90% of 2a (Ar=Ph) after 1 h, see ref 2.
24. Two molecular equivalents of DTBN (based on 4-bromotoluene) were required to completely quench the 2 h reaction.
25. Galli, C. Tetrahedron 1988, 44, 5205-5208.
26. RN1 arylation of imide α-enolates, see: Lotz, G. A.; Palacios, S. M.; Rossi, R. A. Tetrahedron Lett. 1994, 35, 7711-7714.