메뉴 건너뛰기




Volumn 133, Issue 16, 2011, Pages 6449-6457

Rhodium(III)-catalyzed heterocycle synthesis using an internal oxidant: Improved reactivity and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; CATALYST LOADINGS; CATALYTIC CYCLES; DFT CALCULATION; HETEROCYCLE SYNTHESIS; HETEROCYCLES; LIMITING STEP; MECHANISTIC STUDIES; METALATIONS; NEW SYSTEM; OXIDATIVE ADDITIONS; ROOM TEMPERATURE; TERMINAL ALKYNE;

EID: 79955035089     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201143v     Document Type: Article
Times cited : (815)

References (93)
  • 4
    • 33751424969 scopus 로고    scopus 로고
    • For a review on heterocycle synthesis via oxidative addition, see
    • For a review on heterocycle synthesis via oxidative addition, see: Zeni, G; Larock, R. C. Chem. Rev. 2006, 106, 4644
    • (2006) Chem. Rev. , vol.106 , pp. 4644
    • Zeni, G.1    Larock, R.C.2
  • 31
    • 77949381429 scopus 로고    scopus 로고
    • For a recent review on Pd-catalyzed ligand directed C-H functionalization, see
    • For a recent review on Pd-catalyzed ligand directed C-H functionalization, see: Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
    • (2010) Chem. Rev. , vol.110 , pp. 1147
    • Lyons, T.W.1    Sanford, M.S.2
  • 32
    • 77349090183 scopus 로고    scopus 로고
    • For a recent review on Rh-catalyzed C-C bond formation via heteroatom directed C-H bond activation, see
    • For a recent review on Rh-catalyzed C-C bond formation via heteroatom directed C-H bond activation, see: Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
    • (2010) Chem. Rev. , vol.110 , pp. 624
    • Colby, D.A.1    Bergman, R.G.2    Ellman, J.A.3
  • 33
    • 77952573385 scopus 로고    scopus 로고
    • The catalytic cycle can be intercepted prior to C-N bond formation, resulting in hydroarylation, see
    • The catalytic cycle can be intercepted prior to C-N bond formation, resulting in hydroarylation, see: Schipper, D. J.; Hutchinson, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6910
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6910
    • Schipper, D.J.1    Hutchinson, M.2    Fagnou, K.3
  • 34
    • 77957204974 scopus 로고    scopus 로고
    • For a recent and comprehensive review of rhodium(III)-catalyzed formation of heterocycles via annulative processes with internal alkynes, see
    • For a recent and comprehensive review of rhodium(III)-catalyzed formation of heterocycles via annulative processes with internal alkynes, see: Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
    • (2010) Chem.-Eur. J. , vol.16 , pp. 11212
    • Satoh, T.1    Miura, M.2
  • 40
    • 79951846441 scopus 로고    scopus 로고
    • During the preparation of this manuscript, a related redox-neutral approach was reported, see
    • During the preparation of this manuscript, a related redox-neutral approach was reported, see: Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 2350
    • Rakshit, S.1    Grohmann, C.2    Besset, T.3    Glorius, F.4
  • 42
    • 67649488045 scopus 로고    scopus 로고
    • For reviews on Pd-catalyzed oxidative coupling of alkenes, see
    • For reviews on Pd-catalyzed oxidative coupling of alkenes, see: Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5094
    • Chen, X.1    Engle, K.M.2    Wang, D.-H.3    Yu, J.-Q.4
  • 43
    • 43849099094 scopus 로고    scopus 로고
    • For selected recent individual reports
    • Ferreira, E. M.; Zhang, H.; Stoltz, B. M. Tetrahedron 2008, 64, 5987 For selected recent individual reports
    • (2008) Tetrahedron , vol.64 , pp. 5987
    • Ferreira, E.M.1    Zhang, H.2    Stoltz, B.M.3
  • 64
    • 77952570693 scopus 로고    scopus 로고
    • For a redox-neutral method:;;, For oxidative methods see ref 6g-6i
    • For a redox-neutral method: Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908 For oxidative methods see ref 6g-6i.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6908
    • Guimond, N.1    Gouliaras, C.2    Fagnou, K.3
  • 65
    • 0035382925 scopus 로고    scopus 로고
    • For a review on recent isoquinolone synthesis, see
    • For a review on recent isoquinolone synthesis, see: Glushkov, V. A.; Shklyaev, Y. V. Chem. Heterocycl. Compd. 2001, 37, 663
    • (2001) Chem. Heterocycl. Compd. , vol.37 , pp. 663
    • Glushkov, V.A.1    Shklyaev, Y.V.2
  • 72
    • 79955025560 scopus 로고    scopus 로고
    • Trans -stilbene, 3-hexene, and cyclohexene failed to provide the desired 3,4-dihydroisoquinolone
    • Trans -stilbene, 3-hexene, and cyclohexene failed to provide the desired 3,4-dihydroisoquinolone.
  • 74
    • 51949093660 scopus 로고    scopus 로고
    • For studies of alkyne insertion with related cyclometalated substrates, see
    • For studies of alkyne insertion with related cyclometalated substrates, see: Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12414
    • Li, L.1    Brennessel, W.W.2    Jones, W.D.3
  • 91
    • 79955037159 scopus 로고    scopus 로고
    • 3)(Ph)(OAc)]) (ref 33e)
    • 3)(Ph)(OAc)]) (ref 33e).
  • 93
    • 79955011852 scopus 로고    scopus 로고
    • 1H NMR yield
    • 1H NMR yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.