An assessment of late transition metals as hydroamination catalysts in the cyclization of C-propargyl vinylogous amides into pyrroles

Tetrahedron Letters

Volumn 49, Issue 3, 2008, Pages 411-414

  Prior, Allan M ^a   Robinson, Ross S ^a  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE SILVER; AMIDE; CADMIUM ACETATE; CADMIUM CHLORIDE; CADMIUM DERIVATIVE; CADMIUM NITRATE; CADMIUM OXIDE; COPPER ACETATE; COPPER CHLORIDE; COPPER DERIVATIVE; COPPER NITRATE; COPPER OXIDE; MERCURIC NITRATE; MERCURIC OXIDE; MERCURY ACETATE; MERCURY CHLORIDE; PYRROLE DERIVATIVE; SILVER CHLORIDE; SILVER DERIVATIVE; SILVER NITRATE; SILVER OXIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZINC ACETATE; ZINC CHLORIDE; ZINC NITRATE; ZINC OXIDE;

ACIDITY; AMINATION; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; HYDROAMINATION; OXIDATION; REACTION ANALYSIS;

EID: 37249084150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.116     Document Type: Article

References (35)

1. Louie J., and Hartwig J.F. Tetrahedron Lett. 36 (1995) 3609-3612
2. Ma D., and Yao J. Tetrahedron: Asymmetry 7 (1996) 3075-3078
3. Driver M.S., and Hartwig J.F. J. Am. Chem. Soc. 118 (1996) 7217-7218
4. Wolfe J.P., Wagaw S., and Buchwald S.L. J. Am. Chem. Soc. 118 (1996) 7215-7216
5. Robinson R.S., Dovey M.C., and Gravestock D. Eur. J. Org. Chem. 3 (2005) 505-511
6. Wolfe J.P., and Buchwald S.L. J. Org. Chem. 62 (1997) 1264-1267
7. Louie J., Driver M.S., Hamann B.C., and Hartwig J.F. J. Org. Chem. 62 (1997) 1268-1273
8. Nobis M., and Driebßen-Hölscher B. Angew. Chem., Int. Ed. 40 (2001) 3983-3985
9. Howk B.W., Little E.L., Scott S.L., and Whitman G.M. J. Am. Chem. Soc. 76 (1954) 1899-1902
10. Bambirra S., Tsurugi H., van Leusen D., and Hessen B. Dalton Trans. (2006) 1157-1161
11. Anderson L.L., Arnold J., and Bergman R.G. Org Lett. 6 (2004) 2519-2522
12. Lorber C., Choukroun R., and Vendier L. Organometallics 23 (2004) 1845-1850
13. Müller T.E., and Pleier A.-K. J. Chem. Soc., Dalton Trans. (1999) 583-587
14. Kim Y.K., Livinghouse T., and Bercaw J.E. Tetrahedron Lett. 42 (2001) 2933-2935
15. Severin R., and Doye S. Chem. Soc. Rev. 36 (2007) 1407-1420
16. Robinson R.S., Dovey M.C., and Gravestock D. Tetrahedron Lett. 45 (2004) 6787-6789
17. Larock R.C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations (1989), VHC pp 981-988
18. Stahly G.P., Marlett E.M., and Nelson G.E. J. Org. Chem. 48 (1983) 4423-4426
19. 4Cl (five drops) and concentrated in vacuo to yield the crude C-propargyl vinylogous amide as a brown oil, in 80% yield.
20. 1H NMR spectroscopy. All microwave reactions were performed using a CEM Discover laboratory microwave oven.
21. Baldwin J.E., Thomas R.C., Kruse L.I., and Silberman L. J. Org. Chem. 42 (1977) 3846-3852
22. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734-736
23. Refer to Ref. 14 with the exception that 0.2 equiv of catalyst, 100 W of microwave irradiation, and a reaction time of 1 min were utilized.
24. Field L.D., and Ward A.J. J. Organomet. Chem. 681 (2003) 91-97
25. Bochmann M. Organometallics 2: Complexes with Transition Metal-Carbon π-Bonds (2000), Oxford University Press pp 20-21
26. Hultzsch K.C. Org. Biomol. Chem. 3 (2005) 1819-1824
27. Penzien J., Müller T.E., and Lercher J.A. Chem. Commun. (2000) 1753-1754
28. Shanbhag G.V., and Halligudi S.B. J. Mol. Catal. A: Chem. 222 (2004) 223-228
29. Burling S., Field L.D., Messerle B.A., and Turner P. Organometallics 23 (2004) 1714-1721
30. Bodie D., McDaniel D., and Alexander J. Concepts and Models of Inorganic Chemistry. 3rd ed. (1994), John Wiley Sons pp 386-387
31. Pearson R.G. J. Chem. Educ. 45 (1968) 581-587
32. Müller T.E., Grosche M., Herdtweck E., Pleier A.-K., Walter E., and Yan Y.-K. Organometallics 19 (2000) 170-183
33. Martinez P.H., Hultzsch K.I., and Hample F. Chem. Commun. (2006) 2221-2223
34. Uchimaru Y. Chem. Commun. (1999) 1133-1134
35. Ouh L.L., Müller T.E., and Yan Y.K. J. Organomet. Chem. 690 (2005) 3774-3782