An efficient procedure for palladium-catalyzed hydroformylation of aryl/enol triflates

Synthesis

Volumn , Issue 4, 1996, Pages 470-472

  Kotsuki, Hiyoshizo ^a   Datta, Probal Kanti ^a   Suenaga, Hitoshi ^b  

^a KOCHI UNIVERSITY   (Japan)

^b Teikoku Chemical Industry   (Japan)

Author keywords

aryl enol triflates; carbon monoxide; hydroformylation; palladium catalyzed reaction; trioctylsilane

Indexed keywords

BENZENE DERIVATIVE; NAPHTHALENE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029926127     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4246     Document Type: Article

References (26)

1. Stang, P. J.; Hanack, M.; Subramanian, J. R. Synthesis 1982, 85. Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. Ritter, K. Synthesis 1993, 735.
2. Stang, P. J.; Hanack, M.; Subramanian, J. R. Synthesis 1982, 85. Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. Ritter, K. Synthesis 1993, 735.
3. Stang, P. J.; Hanack, M.; Subramanian, J. R. Synthesis 1982, 85. Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. Ritter, K. Synthesis 1993, 735.
4. Stang, P. J.; Hanack, M.; Subramanian, J. R. Synthesis 1982, 85. Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. Ritter, K. Synthesis 1993, 735.
5. Stang, P. J.; Hanack, M.; Subramanian, J. R. Synthesis 1982, 85. Stille, J. K. Angew. Chem. 1986, 98, 504; Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. Ritter, K. Synthesis 1993, 735.
6. Kotsuki, H.; Kobayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1145.
7. Kotsuki, H.; Datta, P. K.; Hayakawa, H.; Suenaga, H. Synthesis 1995, 1348.
8. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum; New York, 1991. Thompson, D. J. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991.
9. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum; New York, 1991. Thompson, D. J. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991.
10. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 7175. Baillargeon, V. P.; Stille, J. K. ibid. 1986, 108, 452.
11. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 7175. Baillargeon, V. P.; Stille, J. K. ibid. 1986, 108, 452.
12. Misumi, Y.; Ishii, Y.; Hidai, M. Chem. Lett. 1994, 695. Misumi, Y.; Ishii, Y.; Hidai, M. Organometallics 1995, 14, 1770.
13. Misumi, Y.; Ishii, Y.; Hidai, M. Chem. Lett. 1994, 695. Misumi, Y.; Ishii, Y.; Hidai, M. Organometallics 1995, 14, 1770.
14. NOTE: This reagent should be handled in a well-ventilated hood because of the potential toxicity. See: Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1992, 57, 3751.
15. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
16. Aldrich Catalogue/Handbook of Fine Chemicals 1994-1995.
17. Sato, T.; Ito, M.; Ohara, T.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 1839.
18. Huffman, J. W.; Wu, M. J.; Joyner, H. H. J. Org. Chem. 1991, 56, 5224.
19. Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785.
20. Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 4607.
21. Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285.
22. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
23. Dolle, R. E.; Schmidt, S. J.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1987, 904. See also: Hansen, R. L. Chem. Abstr. 1968, 68, 21698c.
24. Dolle, R. E.; Schmidt, S. J.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1987, 904. See also: Hansen, R. L. Chem. Abstr. 1968, 68, 21698c.
25. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
26. This order is essential to get good results. Addition of trioctylsilane first resulted in decreased product yields.