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Volumn 356, Issue 8, 2014, Pages 1866-1872

Palladium on carbon-catalyzed one-pot N-arylindole synthesis: Intramolecular aromatic amination, aromatization, and intermolecular aromatic amination

Author keywords

amination; cross coupling; heterogeneous catalysis; indoles; palladium

Indexed keywords


EID: 84901308164     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201301168     Document Type: Article
Times cited : (29)

References (114)
  • 24
    • 7644224020 scopus 로고    scopus 로고
    • 2 and N-heterocyclic carbene with subsequent N-arylation of the resulting indoline in a one-pot manner.
    • 2 and N-heterocyclic carbene with subsequent N-arylation of the resulting indoline in a one-pot manner., R. Omar-Amrani, R. Schneider, Y. Fort, Synthesis 2004, 2527-2534.
    • (2004) Synthesis , pp. 2527-2534
    • Omar-Amrani, R.1    Schneider, R.2    Fort, Y.3
  • 39
    • 0037419001 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1480-1483.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1480-1483
  • 43
    • 77950361971 scopus 로고    scopus 로고
    • Tokuyama et al. described in their total synthesis of PDE-II that an N-Ns-protected 2-bromoaniline derivative could be directly converted to the corresponding N-unprotected indole derivative by the CuI-catalyzed intramolecular amination followed by in-situ removal of the Ns group and aromatization.
    • Tokuyama et al. described in their total synthesis of PDE-II that an N-Ns-protected 2-bromoaniline derivative could be directly converted to the corresponding N-unprotected indole derivative by the CuI-catalyzed intramolecular amination followed by in-situ removal of the Ns group and aromatization., K. Okano, N. Mitsuhashi, H. Tokuyama, Chem. Commun. 2010, 46, 2641-2643.
    • (2010) Chem. Commun. , vol.46 , pp. 2641-2643
    • Okano, K.1    Mitsuhashi, N.2    Tokuyama, H.3
  • 48
  • 52
    • 72049112575 scopus 로고    scopus 로고
    • M. Pal, Synlett 2009, 2896-2912
    • (2009) Synlett , pp. 2896-2912
    • Pal, M.1
  • 54
    • 79952680430 scopus 로고    scopus 로고
    • A. Molnár, Chem. Rev. 2011, 111, 2251-2320
    • (2011) Chem. Rev. , vol.111 , pp. 2251-2320
    • Molnár, A.1
  • 72
    • 77954568800 scopus 로고    scopus 로고
    • We also demonstrated the utility of the Pd/C as the catalyst for the Yamanaka-Larock indole synthesis.
    • We also demonstrated the utility of the Pd/C as the catalyst for the Yamanaka-Larock indole synthesis., Y. Monguchi, S. Mori, S. Aoyagi, A. Tsutsui, T. Maegawa, H. Sajiki, Org. Biomol. Chem. 2010, 8, 3338-3342.
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 3338-3342
    • Monguchi, Y.1    Mori, S.2    Aoyagi, S.3    Tsutsui, A.4    Maegawa, T.5    Sajiki, H.6
  • 73
    • 84901318833 scopus 로고    scopus 로고
    • Djakovitch used heterogeneous Pd/C and Pd-Cu catalysts for the synthesis of indoles from 2-iodoanilines and alkynes
    • Djakovitch used heterogeneous Pd/C and Pd-Cu catalysts for the synthesis of indoles from 2-iodoanilines and alkynes
  • 76
    • 77954284613 scopus 로고    scopus 로고
    • Novak also applied Pd/C for the aromatic amination.
    • Novak also applied Pd/C for the aromatic amination., A. Komáromi, Z. Novák, Adv. Synth. Catal. 2010, 352, 1523-1532.
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 1523-1532
    • Komáromi, A.1    Novák, Z.2
  • 81
    • 70349929617 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5691-5693
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5691-5693
  • 91
    • 33846689629 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 934-936. For iron catalyst, see
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 934-936
  • 93
    • 36749002068 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 8862-8865. For manganese catalyst, see
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8862-8865
  • 102
    • 84901346428 scopus 로고    scopus 로고
    • [24u]
    • [24u]
  • 103
    • 84901346091 scopus 로고    scopus 로고
    • -1, respectively.
    • -1, respectively.
  • 104
    • 84901335994 scopus 로고    scopus 로고
    • The cyclization effectively proceeded using even 1.5 equiv. of NaO-t-Bu in the presence of 10% Pd/C (2 mol%) and DPPF (3 mol%) in mesitylene at 140°C. The low selectivity for the formation of indoline (1) or indole (2) was however achieved, and a mixture of 1 and 2 was obtained in 94% yield in the ratio of 48:52, respectively.
    • The cyclization effectively proceeded using even 1.5 equiv. of NaO-t-Bu in the presence of 10% Pd/C (2 mol%) and DPPF (3 mol%) in mesitylene at 140°C. The low selectivity for the formation of indoline (1) or indole (2) was however achieved, and a mixture of 1 and 2 was obtained in 94% yield in the ratio of 48:52, respectively.
  • 108
    • 84901308917 scopus 로고    scopus 로고
    • The amount of AcOH was determined to be 1.5 equiv., since 1 equiv. out of 2.5 equiv. of NaO-t-Bu should be theoretically consumed during the cyclization to quench the generated hydrogen bromide.
    • The amount of AcOH was determined to be 1.5 equiv., since 1 equiv. out of 2.5 equiv. of NaO-t-Bu should be theoretically consumed during the cyclization to quench the generated hydrogen bromide.
  • 109
    • 63349112681 scopus 로고    scopus 로고
    • L. Joucla, L. Djakovitch, Adv. Synth. Catal. 2009, 351, 673-714. For heterogeneous N-1, C-2 or C-3 site selective arylation of indole, see
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 673-714
    • Joucla, L.1    Djakovitch, L.2
  • 110
    • 79959613210 scopus 로고    scopus 로고
    • L. Diakovitch, N. Batail, M. Genelot, Molecules 2011, 16, 5241-5267; for homogeneous C-2 or C-1 site selective arylation of indole, see
    • (2011) Molecules , vol.16 , pp. 5241-5267
    • Diakovitch, L.1    Batail, N.2    Genelot, M.3
  • 114
    • 84901336552 scopus 로고    scopus 로고
    • [19h]
    • [19h]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.