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Volumn 129, Issue 45, 2007, Pages 13792-13793

Anti-Markovnikov addition of both primary and secondary amines to terminal alkynes catalyzed by the TpRh(C2H4)2/PPH 3 system

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AMINE; BORON DERIVATIVE; RHODIUM COMPLEX;

EID: 36148955757     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075484e     Document Type: Article
Times cited : (92)

References (33)
  • 1
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    • For recent reviews on catalytic hydroamination, see: a
    • For recent reviews on catalytic hydroamination, see: (a) Odom, A. L. Dalton Trans. 2005, 225.
    • (2005) Dalton Trans , pp. 225
    • Odom, A.L.1
  • 8
    • 36148949559 scopus 로고    scopus 로고
    • Product Subclass of 6: Enamines
    • For reviews on the chemistry of imines and enamines, see: a, Molander, M, Ed, Georg Thieme Verlag: Stuttgart
    • For reviews on the chemistry of imines and enamines, see: (a) Sammakia T.; Abramite, J. A.; Summons, M. F. Product Subclass of 6: Enamines. In Science of Synthesis; Molander, M., Ed.; Georg Thieme Verlag: Stuttgart, 2006; pp 405-411.
    • (2006) Science of Synthesis , pp. 405-411
    • Sammakia, T.1    Abramite, J.A.2    Summons, M.F.3
  • 10
    • 0004087670 scopus 로고
    • Rappoport, Z, Ed, Wiley-VCH: New York
    • (c) Kuckländer, U. In The Chemistry of Enamines; Rappoport, Z., Ed.; Wiley-VCH: New York, 1994; pp 523-636.
    • (1994) The Chemistry of Enamines , pp. 523-636
    • Kuckländer, U.1
  • 22
    • 36148985923 scopus 로고    scopus 로고
    • 3 gave the corresponding anti-Markovnikov enamine in 40% yield. In this case, the pyridine ring was essential to obtain the product. Park, Y. J.; Kwon, B.-I.; Ahn, J.-A.; Jun, C.-H. J. Am. Chem. Soc. 2004, 126, 13892.
    • 3 gave the corresponding anti-Markovnikov enamine in 40% yield. In this case, the pyridine ring was essential to obtain the product. Park, Y. J.; Kwon, B.-I.; Ahn, J.-A.; Jun, C.-H. J. Am. Chem. Soc. 2004, 126, 13892.
  • 23
    • 0000321839 scopus 로고    scopus 로고
    • 1H NMR spectra of (E)- and (Z)-2a, see: Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. Tetrahedron Lett. 1985, 26, 139.
    • 1H NMR spectra of (E)- and (Z)-2a, see: Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. Tetrahedron Lett. 1985, 26, 139.
  • 27
    • 0035929431 scopus 로고    scopus 로고
    • 3 catalyst system gave no hydroamination product in our reaction conditions, although Beller and co-workers reported that the system catalyzed the reaction of phenylacetylene with morpholine to give anti-Markovnikov adducts in 15% yield. See: Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
    • 3 catalyst system gave no hydroamination product in our reaction conditions, although Beller and co-workers reported that the system catalyzed the reaction of phenylacetylene with morpholine to give anti-Markovnikov adducts in 15% yield. See: Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
  • 29
    • 36148977029 scopus 로고    scopus 로고
    • 4 (4f,4g) to isolate the corresponding amines. See Supporting Information.
    • 4 (4f,4g) to isolate the corresponding amines. See Supporting Information.
  • 30
    • 33745777313 scopus 로고    scopus 로고
    • For recent reviews on catalytic reactions that proceeded via vinylidene-metal intermediate, see: a
    • For recent reviews on catalytic reactions that proceeded via vinylidene-metal intermediate, see: (a) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 2176
    • Bruneau, C.1    Dixneuf, P.H.2
  • 31
    • 36148985155 scopus 로고    scopus 로고
    • Bruneau, C. In Topics in Organometallic Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer: Berlin, 2004; 11 (Ruthenium Catalysts and Fine Chemistry), pp 125-153.
    • (b) Bruneau, C. In Topics in Organometallic Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer: Berlin, 2004; Vol. 11 (Ruthenium Catalysts and Fine Chemistry), pp 125-153.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.