Triethylborane as an efficient promoter for palladium-catalyzed allylation of active methylene compounds with allyl alcohols

Tetrahedron

Volumn 59, Issue 39, 2003, Pages 7767-7777

  Kimura, Masanari ^a   Mukai, Ryutaro ^a   Tanigawa, Naoko ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Active methylene compounds; Allyl alcohols; Allylation; Catalytic reaction; Palladium; Triethylborane

Indexed keywords

1 METHYL 2,2 BIS(CINNAMYL)ACETOACETATE; 2 ACETYL 2 ALLYLCYCLOPENTANONE; 2 ACETYL 2 CINNAMYLCYCLOPENTANONE; 2 CINNAMYL 2 ACETYLCYCLOHEXANONE; 2 CINNAMYL 2 ETHOXYCARBONYLCYCLOHEXANONE; 2 CINNAMYL 2 FORMYLCYCLOHEXANONE; ALKENE DERIVATIVE; ALLYL ALCOHOL; ALPHA ACETYL ALPHA (2 CYCLOHEXENYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (2,4 PENTADIENYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (ALPHA METHYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (ALPHA,ALPHA DIMETHYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (BETA METHYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (BETA PHENYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA (GAMMA,GAMMA DIMETHYL) GAMMA BUTYROLACTONE; ALPHA ACETYL ALPHA CROTYL GAMMA BUTYROLACTONE; BORANE DERIVATIVE; DIETHYLBORON 2 ACETYL 1 CYCLOHEXENOLATE; PALLADIUM COMPLEX; PHOSPHINE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0042835748     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01234-1     Document Type: Article

References (53)

1. Godleski S.A. Trost B.M., Fleming I., Paquette L.A. Comprehensive Organic Synthesis. Vol. 4:1991;585 Pergamon, Oxford.
2. (a) Trost B.M. Pure Appl. Chem. 64:1992;315.
3. (b) Trost B.M. Angew. Chem. Int., Ed. Engl. 28:1989;1173.
4. (c) Trost B.M. Acc. Chem. Res. 13:1980;385.
5. (a) Tsuji J. Synthesis. 1990;793.
6. (b) Tsuji J., Minami I. Acc. Chem. Res. 20:1987;140.
7. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
8. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
9. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
10. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
11. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
12. Ir-catalyzed allyl alcohols substitution: (a) Takeuchi R., Kashio M. J. Am. Chem. Soc. 120:1998;8647 (b) Takeuchi R., Kashio M. Angew. Chem. Int., Ed. Engl. 36:1997;263. Ni-catalyzed allyl alcohols substitution: (c) Consiglio G., Piccolo O., Roncetti L., Morandini F. Tetrahedron. 42:1986;2043 (d) Buckwalter B.L., Burfitt I.R., Felkin H., Joly-Goudket M., Naemura K., Salomon M.F., Wenkert E., Wovkulich P.M. J. Am. Chem. Soc. 100:1978;6445. Pd-catalyzed carbonylation accompanied by the C-O bond cleavage of allyl alcohols: (e) Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M.J. Org. Chem. 62:1997;2662-2664 (f) Xiao W.-H., Alper H. J. Org. Chem. 63:1998;7939-7944.
13. Atkins K.E., Walker W.E., Manyik R.M. Tetrahedron Lett. 1970;3821.
14. Bergbreiter D.E., Weatherford D.A. J. Chem. Soc. Chem. Commun. 1989;883.
15. Haudegond J.P., Chauvin Y., Commereuc D. J. Org. Chem. 44:1979;3063.
16. Lu X., Lu L., Sun J. J. Mol. Catal. 41:1987;245.
17. Lu X., Jiang X., Tao X. J. Organomet. Chem. 344:1988;109.
18. Sakamoto M., Shimizu I., Yamamoto A. Bull. Chem. Soc. Jpn. 69:1996;1065.
19. Itoh K., Hamaguchi N., Miura M., Nomura M. J. Chem. Soc. Perkin Trans. 1. 1992;2833.
20. Ozawa F., Okamoto H., Kawagishi S., Yamamoto S., Minami T., Yoshifuji M. J. Am. Chem. Soc. 124:2002;10968.
21. (a) Kimura M., Futamata M., Shibata K., Tamaru Y. J. Chem. Soc. Chem. Commun. 2003;124.
22. (b) Tamaru Y., Horino Y., Araki M., Tanaka S., Kimura M. Tetrahedron Lett. 41:2000;5705.
23. (c) Horino Y., Naito M., Kimura M., Tanaka S., Tamaru Y. Tetrahedron Lett. 42:2001;3113.
24. Kimura M., Horino Y., Mukai R., Tanaka S., Tamaru Y. J. Am. Chem. Soc. 123:2001;10401.
25. 0 species; in press Kimura M., Shimizu M., Shibata K., Tazoe M., Tamaru Y. Angew. Chem. Int. Ed. 42:2003;3392.
26. 0 species; in press Kimura M., Shimizu M., Shibata K., Tazoe M., Tamaru Y. Angew. Chem. Int. Ed. 42:2003;3392.
27. Stary I., Stara I.G., Kocovsky P. Tetrahedron Lett. 34:1993;179.
28. Bordwell F.G., Bares J.E., Bartmess J.E., McCollum G.J., van der Puy M., Vanier N.R., Matthews W.S. J. Org. Chem. 42:1977;326.
29. Smith M.B., March J. Advanced Organic Chemistry. 2001;Wiley, New York. pp. 330-331.
30. Values estimated by using Advanced Chemistry Development Software V4.67.
31. Iglesias E. J. Org. Chem. 68:2003;2680.
32. Emilia I. New J. Chem. 26:2002;1352.
33. Pihlaja K., Seilo M. Acta Chem. Scand. 23:1969;3003.
34. Yorimitsu H., Nakamura T., Shinokubo H., Oshima K., Omoto K., Fujimoto H. J. Am. Chem. Soc. 122:2000;11041.
35. Toporcer L.H., Dessy R.E., Green S.I.E. Inorg. Chem. 4:1965;1649.
36. (a) van Leeuwen P.W.N.M., Kamer P.C., Reek J.N.H., Dierkes P. Chem. Rev. 100:2000;2741.
37. (b) Zhang Z., Qian H., Longmire J., Zhang X. J. Org. Chem. 65:2000;6223.
38. (c) van Haaren R.J., van Strijdonck G.P.F., Oevering H., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M. J. Inorg. Chem. 2001;837.
39. (d) Ogasawara M., Takizawa K., Hayashi T. Organometallics. 21:2002;4853.
40. Ainsworth C. Organic Synthesis. Coll. Vol. 4:1963;Wiley, New York. p 536.
41. Krafft M.E., Boñaga L.V.R., Wright J.A., Hirosawa C. J. Org. Chem. 67:2002;1233.
42. Zhang S.-W., Mitsudo T., Kondo T., Watanabe Y. J. Organomet. Chem. 450:1993;197.
43. Curran D.P., Seong C.M. Tetrahedron. 48:1992;2175.
44. Grigg R., Malone J.F., Mitchell T.R.B., Ramasubbu A., Scott R.M. J. Chem. Soc. Perkin Trans. 1. 1984;1745.
45. Fu Y., Hammarström L.G.J., Miller T.J., Fronczek F.R., McLaughlin M.L., Hammer R.P. J. Org. Chem. 66:2001;7118.
46. Shing T.K.M., Li L.-H., Narkunan K. J. Org. Chem. 62:1997;1617.
47. Hirao T., Yamada N., Ohshiro Y., Agawa T. J. Organomet. Chem. 236:1982;409.
48. Riering H., Schaefer H. J. Chem. Ber. 127:1994;859.
49. Fraga C.A.M., Barreiro E.J. Synth. Commun. 25:1995;1133.
50. Masuyama Y., Yamada K., Shimizu S., Kurusu Y. Bull. Chem. Soc. Jpn. 62:1989;2913.
51. Teixeira L.H.P., de Souza M.C.B.V., Ramos M.C.K.V., de A. Neto F.R., Barreiro E.J., Fraga C.A.M. Synth. Commun. 32:2002;505.
52. King J.F., Rathore R., Lam J.Y.L., Guo Z.R., Klassen D.F. J. Am. Chem. Soc. 114:1992;3028.
53. Caló V., Fiandanese V., Nacci A., Volpe A. Tetrahedron. 52:1996;2155.