Intermolecular coupling of isomerizable alkenes to heterocycles via rhodium-catalyzed C-H bond activation

Journal of the American Chemical Society

Volumn 124, Issue 47, 2002, Pages 13964-13965

  Tan, Kian L ^a,b   Bergman, Robert G ^a,b   Ellman, Jonathan A ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALUMINUM DERIVATIVE; AMMONIUM CHLORIDE; BENZIMIDAZOLE DERIVATIVE; CARBENOID; CARBON; COPPER CHLORIDE; HYDROGEN; PYRROLE DERIVATIVE; RHODIUM; SCANDIUM; ZINC CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CYCLIZATION; ISOMERISM; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ALKENES; BENZIMIDAZOLES; CATALYSIS; HETEROCYCLIC COMPOUNDS; ISOMERISM; RHODIUM;

EID: 0037184456     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0281129     Document Type: Article

References (22)

1. (a) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
2. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. (c) Jia, C. G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
4. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3.
5. (e) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1699-1712.
6. (f) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
7. (a) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
8. (b) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185.
9. (c) Ofele, K. J. Organomet. Chem. 1968, 12, 42.
10. (c) Wanzlick, H. W.; Schonher H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
11. (d) For a review of NHC used as ligands in catalysis see: Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1291.
12. (a) Cavell and co-workers were the first to show that NHCs undergo stoichiometric reductive elimination at a metal center: McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029.
13. (b) McGuinness, D. S.; Cavell, K. J.; Yates, B. F. Chem. Commun. 2001, 355.
14. (c) McGuinness. D. S.; Cavell, K. J.; Yates, B. F.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 2001, 123, 8317.
15. (d) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 3202.
16. Fujiwara and co-workers have shown that certain heterocycles undergo C-H coupling with activated alkynes: Lu, W. J.; Jia, C. G.; Kitamura, T.; Fujiwara, Y. Org. Lett. 2000, 2, 2927.
17. Complete list of additives screened available in Supporting Information.
18. Kocher, C.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 261.
19. Regiochemistry of the bis-alkylated purine was determined by X-ray crystallography. X-ray diffraction data are available in Supporting Information.
20. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, ASAP June 21, 2002.
21. A small amount of the branched isomer was isolated from the reaction. GC-MS analysis of the crude mixture showed a 25:1 linear:branched ratio.
22. At the reaction completion some styrene remains, indicating that poor conversion did not simply result from consumption of styrene.