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Volumn 39, Issue 30, 1998, Pages 5421-5424

A new method for the synthesis of nitrogen heterocycles via palladium catalyzed intramolecular hydroamination of allenes

Author keywords

Allenes; Cyclization; Nitrogen beterocycles; Palladium

Indexed keywords

ALLENE DERIVATIVE; HETEROCYCLIC NITRO COMPOUND; NITROGEN DERIVATIVE; PALLADIUM;

EID: 0032560834     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01044-2     Document Type: Article
Times cited : (140)

References (23)
  • 1
    • 0029902948 scopus 로고    scopus 로고
    • and references cited therein
    • 1. For reviews of transition metal catalyzed hydroamination, see (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306. and references cited therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9295-9306
    • Li, Y.1    Marks, T.J.2
  • 2
    • 0000428298 scopus 로고
    • Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
    • (b) Savoia, D. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; vol. E21e, pp 5356-5394.
    • (1995) Methods of Organic Chemistry (Houben-Weyl) , vol.E21E , pp. 5356-5394
    • Savoia, D.1
  • 3
    • 0000959614 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • (c) Larock, R. C.; Leong, W.W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; vol. 4, pp269-327.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 269-327
    • Larock, R.C.1    Leong, W.W.2
  • 4
    • 0001329983 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • 2. (a) Harding, K. E.; Tiner, T.H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; vol. 4, pp 363-421.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 363-421
    • Harding, K.E.1    Tiner, T.H.2
  • 6
    • 0010423366 scopus 로고
    • Heimchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
    • (c) Orena, M. In In Methods of Organic Chemistry (Houben-Weyl); Heimchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; vol. E21e, pp 5291-5355.
    • (1995) Methods of Organic Chemistry (Houben-Weyl) , vol.E21E , pp. 5291-5355
    • Orena, M.1
  • 9
    • 0000453966 scopus 로고
    • 4. Palladium catalyzed intermolecular hydroaminations have been reported. See, (a) Coulson, D. R. J. Org. Chem. 1973, 38, 1483-1490.
    • (1973) J. Org. Chem. , vol.38 , pp. 1483-1490
    • Coulson, D.R.1
  • 13
    • 0010503306 scopus 로고    scopus 로고
    • Formic acid and chloroacetic acid also exhibited similar activation effect on the reaction rate and chemical yield. However, trifluoroacetic acid and CSA did not work well
    • 6. Formic acid and chloroacetic acid also exhibited similar activation effect on the reaction rate and chemical yield. However, trifluoroacetic acid and CSA did not work well.
  • 15
    • 0003441482 scopus 로고
    • John Wiley & Sons: New York
    • 8. About the formation of 1,3-dienes from π-allylpalladium species, see, (a) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995, pp 356-363.
    • (1995) Palladium Reagents and Catalysts , pp. 356-363
    • Tsuji, J.1
  • 17
    • 0010421749 scopus 로고    scopus 로고
    • Acetic acid would enhance the rate of formation of hydridopalladium(II) species. Presumably, the direct formation of hydridopalladium(II) species from allenic amine derivatives and Pd(0) is sluggish
    • 9. Acetic acid would enhance the rate of formation of hydridopalladium(II) species. Presumably, the direct formation of hydridopalladium(II) species from allenic amine derivatives and Pd(0) is sluggish.
  • 18
    • 0000561761 scopus 로고
    • We also proposed the hydropalladation mechanism for the intramolecular reaction. See also ref. 5
    • 10. Trost and Gerusz proposed hydropalladation mechanism for the reaction of allenes with active methylene compounds: J. Am. Chem Soc. 1995, 117, 5156-5157. We also proposed the hydropalladation mechanism for the intramolecular reaction. See also ref. 5.
    • (1995) J. Am. Chem Soc. , vol.117 , pp. 5156-5157
  • 19
    • 85064451923 scopus 로고
    • 11. Gallagher et al. proposed nucleophilic addition to allenes activated by arylpalladium(II) species as an alternative mechanism. However, this mechanism cannot account for the formation of 1,3-diene. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85-87.
    • (1993) Synlett , pp. 85-87
    • Davies, I.W.1    Scopes, D.I.C.2    Gallagher, T.3
  • 20
    • 33845555454 scopus 로고
    • 12. Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451. See also Pugin, P.; Venanzi, L. M. J. Organomet. Chem. 1981, 214, 125-133.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2444-2451
    • Hegedus, L.S.1    McKearin, J.M.2
  • 21
    • 0001132729 scopus 로고
    • 12. Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451. See also Pugin, P.; Venanzi, L. M. J. Organomet. Chem. 1981, 214, 125-133.
    • (1981) J. Organomet. Chem. , vol.214 , pp. 125-133
    • Pugin, P.1    Venanzi, L.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.