메뉴 건너뛰기




Volumn 132, Issue 30, 2010, Pages 10565-10569

Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE INSERTIONS; BENZAMIDES; C-H ACTIVATION; CARBOXAMIDES; GOOD YIELD; MEDICINAL CHEMISTRY; METALATIONS; RHODIUM-CATALYZED; SILYL ETHERS; UNSYMMETRICAL;

EID: 77955035554     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103776u     Document Type: Article
Times cited : (547)

References (44)
  • 3
    • 77955014834 scopus 로고    scopus 로고
    • For recent examples, see
    • For recent examples, see
  • 9
  • 17
    • 77955016847 scopus 로고    scopus 로고
    • For a recent review of rhodium catalyzed C-H activation in C-C bond formation see
    • For a recent review of rhodium catalyzed C-H activation in C-C bond formation see
  • 19
    • 77955032108 scopus 로고    scopus 로고
    • For recent examples, see
    • For recent examples, see
  • 22
    • 77955017273 scopus 로고    scopus 로고
    • For a recent stoichiometric example see
    • For a recent stoichiometric example see
  • 29
    • 69349098824 scopus 로고    scopus 로고
    • For an additional rhodium catalyzed cyclization by Fagnou, see
    • For an additional rhodium catalyzed cyclization by Fagnou, see: Guimond, N. and Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 12050
    • Guimond, N.1    Fagnou, K.2
  • 30
    • 77955018552 scopus 로고    scopus 로고
    • For a review of isoquinolone synthesis, see
    • For a review of isoquinolone synthesis, see
  • 32
    • 43849112641 scopus 로고    scopus 로고
    • This has been suggested in palladium C-H functionalization; see
    • This has been suggested in palladium C-H functionalization; see Lafrance, M., Lapointe, D., and Fagnou, K. Tetrahedron 2008, 64, 6015
    • (2008) Tetrahedron , vol.64 , pp. 6015
    • Lafrance, M.1    Lapointe, D.2    Fagnou, K.3
  • 33
    • 77955015930 scopus 로고    scopus 로고
    • Similar reactivity was observed by Miura and Satoh when examining 2-aryl oxazole substrates; see ref 8c
    • Similar reactivity was observed by Miura and Satoh when examining 2-aryl oxazole substrates; see ref 8c
  • 34
    • 77955038091 scopus 로고    scopus 로고
    • I -Pr and t -Bu benzamides provide no cycloadduct under these conditions
    • I -Pr and t -Bu benzamides provide no cycloadduct under these conditions
  • 35
    • 77955026434 scopus 로고    scopus 로고
    • N -acyl benzyl amines do not undergo the cycloaddition under these conditions
    • N -acyl benzyl amines do not undergo the cycloaddition under these conditions
  • 36
    • 77955043895 scopus 로고    scopus 로고
    • Under these conditions, N -methylpyridine-3-carboxamide and N,2-dimethyloxazole-4-carboxamide afford cycloadduct in 0% and 8% yield, respectively
    • Under these conditions, N -methylpyridine-3-carboxamide and N,2-dimethyloxazole-4-carboxamide afford cycloadduct in 0% and 8% yield, respectively
  • 37
    • 84855627640 scopus 로고    scopus 로고
    • 2 conditions
    • 2 conditions
  • 38
    • 77955044089 scopus 로고    scopus 로고
    • Terminal alkynes are not tolerated under the current reaction conditions
    • Terminal alkynes are not tolerated under the current reaction conditions
  • 39
    • 77955034901 scopus 로고    scopus 로고
    • Acetic acid is generated during the course of the reaction and the Cu salt is used as its hydrate, presumably providing the necessary water and acid to lead to hydrolysis of the acetal
    • Acetic acid is generated during the course of the reaction and the Cu salt is used as its hydrate, presumably providing the necessary water and acid to lead to hydrolysis of the acetal
  • 40
    • 77955034059 scopus 로고    scopus 로고
    • This deuteration experiment was also conducted on N- t -Bu benzamide. In the absence of alkyne, no deuterium incorporation was observed after 16 h under these conditions suggesting the sterics of the tert -butyl group negatively affects its ability to metalate by rhodium. This also suggests that metalation occurs on nitrogen rather than oxygen
    • This deuteration experiment was also conducted on N- t -Bu benzamide. In the absence of alkyne, no deuterium incorporation was observed after 16 h under these conditions suggesting the sterics of the tert -butyl group negatively affects its ability to metalate by rhodium. This also suggests that metalation occurs on nitrogen rather than oxygen
  • 41
    • 77955039979 scopus 로고    scopus 로고
    • The apparent reversed regioselectivity in product 3u seems to contradict this model; further studies to address this dichotomy are ongoing
    • The apparent reversed regioselectivity in product 3u seems to contradict this model; further studies to address this dichotomy are ongoing.
  • 42
    • 77955032484 scopus 로고    scopus 로고
    • During the preparation and review of this manuscript, similar and complementary studies leading to isoquinolone synthesis were reported by the groups of Keith Fagnou and Masahiro Miura; see
    • During the preparation and review of this manuscript, similar and complementary studies leading to isoquinolone synthesis were reported by the groups of Keith Fagnou and Masahiro Miura; see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.