Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3543-3546

  Wang, Zhongren ^a   Skerlj, Renato T ^a   Bridger, Gary J ^a  

^a GENZYME CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; HYDRAZIDE DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033617328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00561-4     Document Type: Article

References (16)

1. 1. a) Ultee, M. E.; Bridger, G. J.; Abrams, M. J.; Longley, C. B.; Burton, C. A.; Larson, S.; Henson, G.; Padmanabhan, S.; Gaul, F.; Schwartz, D. J. Nucl. Med. 1997, 38, 133.
2. b) Bridger, G. J.; Abrams, M. J.; Padmanabhan, S.; Gaul, F.; Larson, S.; Henson, G.; Schwartz, D. A.; Longley, C. B.; Burton, C. A.; Ultee, M. E. Bioconjugate Chem. 1996, 7, 255.
3. 2. a) Old, D.W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
4. b) Sadighi, J. P.; Harris, M. C. Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327.
5. c) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359.
6. d) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
7. e) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
8. 3. a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
9. b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694.
10. c) For a review, see: Hartwig, J. F. Synlett 1997, 329.
11. 4. For an example of an intramolecular amidation, see: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
12. 5. For examples of selective aminations see: a) Hong, Y.; Senanayake, C. H.; Xiang, T.; Vandenbossche, C. P.; Tanoury, G. J.; Bakale, R. P.; Wald, S. A. Tetrahedron Lett. 1998, 39, 3121. b) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1997, 38, 2287.
13. 5. For examples of selective aminations see: a) Hong, Y.; Senanayake, C. H.; Xiang, T.; Vandenbossche, C. P.; Tanoury, G. J.; Bakale, R. P.; Wald, S. A. Tetrahedron Lett. 1998, 39, 3121. b) Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1997, 38, 2287.
14. 4. It should be noted that aryl chlorides failed to couple under the reaction conditions.
15. 3 (1.0 eq), then evacuated and purged with nitrogen (repeated three times). Degassed toluene was added (to give a 0.5 M solution of aryl bromide), the vial was sealed and heated to 100 °C with stirring for 16 h. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane, filtered and concentrated. The crude product was then purified by flash column chromatography on silica gel or basic alumina.
16. 8. Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; Lemaire, M. Tetrahedron Lett. 1998, 39, 2559.