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Volumn 13, Issue 13, 2011, Pages 3490-3493

Nickel(0)-catalyzed cyclization of N -benzoylaminals for isoindolinone synthesis

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINE; BENZYLAMINE DERIVATIVE; ISOINDOLE DERIVATIVE; NICKEL;

EID: 79959732695     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201248c     Document Type: Article
Times cited : (66)

References (52)
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    • Gabriel, S. Ber. 1885, 18, 3470
    • (1885) Ber. , vol.18 , pp. 3470
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  • 28
    • 51949105698 scopus 로고    scopus 로고
    • Enantioenriched aminals can also be prepared by the addition of alcohol to an imine. See
    • Enantioenriched aminals can also be prepared by the addition of alcohol to an imine. See: Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12216
    • Li, G.1    Fronczek, F.R.2    Antilla, J.C.3
  • 29
    • 42149172683 scopus 로고    scopus 로고
    • Aminals can also be prepared from the amide and acetal. See
    • Aminals can also be prepared from the amide and acetal. See: Downey, C. W.; Johnson, M. W.; Tracy, K. J. J. Org. Chem. 2008, 73, 3299
    • (2008) J. Org. Chem. , vol.73 , pp. 3299
    • Downey, C.W.1    Johnson, M.W.2    Tracy, K.J.3
  • 36
    • 79959694837 scopus 로고    scopus 로고
    • See Supporting Information for full experimental details.
    • See Supporting Information for full experimental details.
  • 37
    • 33646501936 scopus 로고    scopus 로고
    • The Arndtsen group has attributed amide formation to thermal decomposition of the iminium ion. See
    • The Arndtsen group has attributed amide formation to thermal decomposition of the iminium ion. See: Siamaki, A. R.; Arndtsen, B. A J. Am. Chem. Soc. 2006, 128, 6050
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6050
    • Siamaki, A.R.1    Arndtsen, B.A.2
  • 38
    • 79959687282 scopus 로고    scopus 로고
    • 2 and no Ni(0) catalyst, the cyclization of N -(p -methoxybenzoyl)aminal 1i resulted in only 3% yield of isoindolinone 3i.
    • 2 and no Ni(0) catalyst, the cyclization of N -(p -methoxybenzoyl)aminal 1i resulted in only 3% yield of isoindolinone 3i.
  • 39
    • 79959739200 scopus 로고    scopus 로고
    • 2 resulted in complete decomposition of aminal 1a. Significant decomposition of aminal 1a to amide 4 was observed under these conditions, but no isoindolinone 3a was observed.
    • 2 resulted in complete decomposition of aminal 1a. Significant decomposition of aminal 1a to amide 4 was observed under these conditions, but no isoindolinone 3a was observed.
  • 40
    • 79959722937 scopus 로고    scopus 로고
    • This result is consistent with observations of Doyle's Ni-catalyzed cross-coupling of related aminal substrates. See ref 13.
    • This result is consistent with observations of Doyle's Ni-catalyzed cross-coupling of related aminal substrates. See ref 13.
  • 41
    • 0035354658 scopus 로고    scopus 로고
    • Similar mechanistic quandries have been proposed for related Pd-catalyzed cyclizations. See
    • Similar mechanistic quandries have been proposed for related Pd-catalyzed cyclizations. See: Martín-Matute, B.; Mateo, C.; Cárdenas, D.; Echavarren, A. Chem.-Eur. J. 2001, 7, 2341
    • (2001) Chem.-Eur. J. , vol.7 , pp. 2341
    • Martín-Matute, B.1    Mateo, C.2    Cárdenas, D.3    Echavarren, A.4
  • 52
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    • Significant intramolecular KIEs have been observed in similar reactions that do proceed via C-H activation. See
    • Significant intramolecular KIEs have been observed in similar reactions that do proceed via C-H activation. See: Hennessey, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12084
    • Hennessey, E.J.1    Buchwald, S.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.