Functionalization of alkynes catalyzed by t-Bu-P4 base

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1090-1092

  Imahori, Tatsushi ^a   Hori, Chieko ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkynes; Enamines; Nucleophilic addition; Organic catalysis; Phosphazenes; Propargyl alcohols

Indexed keywords

ACETYLENE DERIVATIVE; ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; CARBONYL DERIVATIVE; DIISOPROPYLAMINE; DIMETHYL SULFOXIDE; ENAMINE; ETHER DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIMERIZATION; STRUCTURE ANALYSIS;

EID: 5144232802     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404076     Document Type: Article

References (30)

1. a) E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349;
2. b) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. Int. Ed. 2002, 41, 4563;
3. c) R. Casado, M. Contel, M. Laguna, P. Romero, S. Sanz, J. Am. Chem. Soc. 2003, 125, 11925;
4. d) L. Ackermann, Organometallics 2003, 22, 4367 and references cited therein.
5. a) D. Tzalis, C. Koradin, P. Knöchel, Tetrahedron Lett. 1999, 40, 6193;
6. b) A. L. Rodriguez, C. Koradin, W. Dohle, P. Knochel, Angew., Chem. Int Ed. 2000, 39, 2488;
7. c) C. Koradin, W. Dohle, A. L. Rodriguez, B. Schmid, P. Knochel, Tetrahedron 2003, 59, 1571.
8. a) R. Schwesinger, H. Schlemper, Angew. Chem. Int. Ed. Engl. 1987, 26, 1167;
9. b) R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H. G. von Schnering, L. Walz, Liebigs Ann. 1996, 1055.
10. a) H. T. Momdani, R. C. Hartley, Tetrahedron Lett. 2000, 41, 747;
11. b) D. Seebach, A. K. Beck, A. Studer, in: Modern Synthetic Methods 1995, (Eds.: B. Ernst, C. Leumann), VCH, Weinheim, 1995, Vol. 7, pp. 1-178.
12. a) G. A. Kraus, N. Zhang, J. G. Verkade, M. Nagarajan, P. B. Kisanga, Org. Lett. 2000, 2, 2409;
13. b) T. Pietzonka, D. Seebach, Chem. Ber. 1991, 124, 1837;
14. c) T. Pietzonka, D. Seebach, Angew. Chem. Int. Ed. Engl. 1993, 32, 716;
15. d) I. Leito, T. Rodima, I. A. Koppel, R. Schwesinger, V. M. Vlasov, J. Org. Chem. 1997, 62, 8479;
16. f) H. Schlaad, H. Kukula, J. Rudloff, I. Below, Macromolecules, 2001, 34, 4302.
17. T. Imahori, Y. Kondo, J. Am. Chem. Soc, 2003, 125, 8082.
18. a) B. M. Trost, Science 1991, 254, 1471;
19. b) K. C. Nicolaou, W. M. Dai, S. C. Tsay, V. A. Estevez, W. Wrasidlo, Science 1992, 256, 1172.
20. a) B. M. Trost, D. Toste, A. Pinkerton, Chem. Rev. 2001, 101, 2067;
21. b) C. Bruneau, P. H. Dixneuf, Acc. Chem. Res. 1999, 32, 311.
22. a) M. Nishiura, N. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184-1185;
23. b) M. Rubina, V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 11107;
24. c) Y. Nishibayashi, M. Yamanashi, I. Wakiji, M. Hidai, Angew. Chem. Int. Ed. 2000, 39, 2909;
25. d) A. Haskel, T. Straub, A. K. Dash, S. Eisen, J. Am. Chem. Soc. 1999, 121, 3014.
26. a) X. Li, G. Lu, W. H. Kwok, A. S. C. Chan, J. Am. Chem, Soc. 2002, 124, 12636;
27. b) C. Wei, C.-J. Li, Green Chemistry 2002, 4, 39.
28. nd edn., Elsevier, Amsterdam, 1988.
29. D. Tzalis, P. Knochel, Angew. Chem. Int. Ed. 1999, 38, 1463.
30. Recently a catalytic alkynylation of carbonyl compounds using quaternary ammonium hydroxide base was reported: T. Ishikawa, T. Mizuta, K. Hagiwara, T. Aikawa, T. Kudo, S. Saito, J. Org. Chem. 2003, 68, 3702.