Catalytic Hunsdiecker reaction and one-pot catalytic Hunsdiecker-Heck strategy: Synthesis of α,β-unsaturated aromatic halides, α- (dihalomethyl)benzenemethanols, 5-aryl-2,4-pentadienoic acids, dienoates and dienamides

Tetrahedron

Volumn 56, Issue 10, 2001, Pages 1369-1377

  Naskar, Dinabandhu ^a   Roy, Sujit ^a  

^a Organic Division II   (India)

Author keywords

Catalytic Hunsdiecker reaction; Heck coupling; Unsaturated aromatic halides

Indexed keywords

ACETONITRILE; ACETYLACETONE; ANTIMONY DERIVATIVE; AROMATIC CARBOXYLIC ACID; AROMATIC COMPOUND; DICHLOROETHANE; HALIDE; METHANOL DERIVATIVE; PALLADIUM COMPLEX; SUCCINIMIDE DERIVATIVE; TETRABUTYLAMMONIUM; TRIETHYLAMINE; TRIFLUOROACETIC ACID; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DECARBOXYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0343114367     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01035-2     Document Type: Article

References (47)

1. (a) Borodin, B. Liebigs Ann. 1861, 119, 121.
2. (b) Hunsdiecker, H. C. Chem. Ber. 1942, 75, 291.
3. (c) Chrich, D. In Comprehensive Organic Synthesis; Trost, B. M., Steven, V. L. Eds.; Pergamon: Oxford, 1991; Vol. 7, pp. 723-734.
4. (d) Sheldon, R. A.; Kochi, J. K. Org. React. (NY) 1972, 19, 326.
5. (e) Mckillop, A.; Bromley; Taylor, E. C. J. Org. Chem. 1969, 34, 1172.
6. (f) Kochi, J. K. J. Am. Chem. Soc. 1965, 87, 2500.
7. (g) Cristol, S. J.; Firth, W. C., Jr. J. Org. Chem. 1961, 26, 280.
8. (h) Hassner, A.; Stumer, C. Organic Syntheses based on Name and Unnamed Reactions; Pergamon: Oxford, 1994; p. 183.
9. Trost B.M. Angew. Chem., Int. Ed. Engl. 34:1995;259.
10. Typical yield 18% from silver cinnamate/bromine: Johnson, R. J.; Ingham, R. K. Chem. Rev. 1956, 56, 219. Improved yield in oxidative halo decarboxylation using stoichiometric PhIO/NBS/acid/60°C: Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543.
11. Typical yield 18% from silver cinnamate/bromine: Johnson, R. J.; Ingham, R. K. Chem. Rev. 1956, 56, 219. Improved yield in oxidative halo decarboxylation using stoichiometric PhIO/NBS/acid/60°C: Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543.
12. (a) Chowdhury, S.; Roy, S. Tetrahedron Lett. 1996, 37, 2623.
13. (b) Chowdhury, S.; Roy, S. J. Org. Chem. 1997, 62, 199.
14. Garner, C. D.; Hughes, B. In Adv. Inorg. Chem. Radiochem.; Emeleus, H. J., Sharpe, A. G., Eds.; 1975, Vol. 17, pp. 1-47.
15. The addition of bromine to the double becomes the major reaction in polar solvent like tetrachloroethane, nitromethane: Pizey, J. S. Synthetic Reagents; Ellis Horwood: Chichester, UK, 1974; Vol. 2, pp. 1-64.
16. Naskar D., Chowdhury S., Roy S. Tetrahedron Lett. 39:1998;699.
17. (a) Weberl, L. M.; Headen, N.; Elslager, E. F. J. Med. Chem. 1967, 10, 366.
18. (b) Bittner, S.; Gorodetsky, M.; Har-Paz, I.; Mizarahi, Y.; Richmond, A. E. Phytochemistry 1977, 16, 143.
19. (c) Oritani, T.; Nanjyo, M.; Fujita, M.; Yamashita, K. Agric. Biol. Chem. 1978, 42, 1437.
20. (d) Chem. Abstr. 1978, 89, 163269.
21. (a) Dahiya, J. S.; Woods, D. L.; Tewari, J. P. Phytochemistry 1988, 28, 2159.
22. (b) Miyakado, M.; Nakayama, I.; Ohno, N. Insecticides of Plant Origin; American Chemical Society: Washington, 1989; Chapter 13, pp. 173-187.
23. (c) Nakatani, N.; Inatani, R.; Ohta, H.; Nishioka, A. Environ. Health Perspect. 1986, 67, 135.
24. (a) Crombie, L.; Pattende, G.; Stemp, G. Phytochemistry 1977, 16, 1437.
25. (b) Huang, Y. Z.; Shi, L.; Yang, J.; Zhang, J. Tetrahedron Lett. 1987, 28, 2159.
26. (c) Myrboh, B.; Asokan, C. V.; Ila, H.; Junjappa, H. Synthesis 1984, 50 and references therein.
27. (a) Huang, Y. Z.; Mo, X. S.; Wang, L. Tetrahedron Lett. 1998, 39, 419.
28. (b) Abarbri, M.; Parrain, J. L.; Duchene, A. Synth. Commun. 1998, 28, 239.
29. (c) Lewis, N.; McKen, P. W.; Taylor, R. J. K. Synlett 1991, 898.
30. (d) Babudri, F.; Fiandanese, F.; Naso, V.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067.
31. (e) Bernabeu, M. C.; Chinchilla, R.; Najera, C. Tetrahedron Lett. 1995, 36, 3901.
32. (f) Crombie, L.; Hobbs, A. J. W.; Horsham, M. A. Tetrahedron Lett. 1987, 28, 4875.
33. (g) Crombie, L.; Horsham, M. A.; Blade, R. J. Tetrahedron Lett. 1987, 28, 487.
34. (a) For review, see, Meijere, A. D.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
35. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
36. (c) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1975, 40, 1083.
37. (a) Tsuboi, S.; Takeda, A. Tetrahedron Lett. 1979, 1043.
38. (b) Normant, H.; Fugeas, C. Compt. Rend. 1964, 258, 2846.
39. (c) Wenkert, E.; Hagaman, D. W.; Lewis, R. B.; Schell, F. M. J. Am. Chem. Soc. 1971, 93, 6271.
40. (a) Chatterjee, A.; Dutta, C. P. Tetrahedron Lett. 1966, 1797.
41. (b) Okogun, J. I.; Khong, D. E. U. J. Chem. Soc., Perkin Trans. 1 1974, 2195.
42. Parrod, J.; Elles, J. Compt. Rend. 1956, 243, 1040; Chem. Abstr. 1957, 51, 6641e.
43. Parrod, J.; Elles, J. Compt. Rend. 1956, 243, 1040; Chem. Abstr. 1957, 51, 6641e.
44. Roy S., Das I., Bhanuprakash K., Gupta B.D. Tetrahedron. 50:1994;1847.
45. Karpaty M. Bull. Soc. Chim. Fr. 1971;1731.
46. Lee G.C.M., Tobin B., Holmes J.M., Harbourt D.M., Garst M.E. J. Am. Chem. Soc. 112:1990;9330.
47. Johnson M.D., Meeks B.S. Chem. Commun. 1970;1027.