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Volumn 352, Issue 14-15, 2010, Pages 2531-2537

A general and practical access to chiral quinoxalinones with low copper-catalyst loading

Author keywords

copper catalyst; coupling reactions; low catalyst loading; quinoxalinones; Ullmann reaction

Indexed keywords


EID: 78349253782     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000323     Document Type: Article
Times cited : (46)

References (46)
  • 1
    • 78349276726 scopus 로고    scopus 로고
    • Recent reviews on copper-catalyzed Ullmann-type coupling reaction, see
    • Recent reviews on copper-catalyzed Ullmann-type coupling reaction, see
  • 3
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    • Angew. Chem. Int. Ed. 2009, 48, 6954 - 6971
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6954-6971
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    • Angew. Chem. Int. Ed. 2006, 45, 7134 -7186
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7134-7186
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    • 2198 and references cited therein.
    • I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127 - 2198 and references cited therein.
    • (2004) Chem. Rev. , vol.104 , pp. 2127
    • Nakamura, I.1    Yamamoto, Y.2
  • 20
    • 78349254021 scopus 로고    scopus 로고
    • Limited examples have appeared for the low catalyst loading copper-mediated reaction. Taillefer et al. showed that only 10 ppm of Cu was enough for the coupling at 80°C of PhI and phenols, see
    • Limited examples have appeared for the low catalyst loading copper-mediated reaction. Taillefer et al. showed that only 10 ppm of Cu was enough for the coupling at 80°C of PhI and phenols, see
  • 21
    • 78349274194 scopus 로고    scopus 로고
    • 505, and references cited therein. Bolm recently reported the C-N bond coupling reaction using a part-per-million catalyst loading with an excess (20 mol%) of ligand, see
    • A. Ouali, J.-F. Spindler, H.-J. Cristau, M. Taillefer, Adv. Synth. Catal. 2006, 348, 449 - 505, and references cited therein. Bolm recently reported the C-N bond coupling reaction using a part-per-million catalyst loading with an excess (20 mol%) of ligand, see
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 449
    • Ouali, A.1    Spindler, J.-F.2    Cristau, H.-J.3    Taillefer, M.4
  • 23
    • 70349929617 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5691 - 5693.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5691-5693
  • 34
    • 78349288251 scopus 로고    scopus 로고
    • See Supporting Information.
    • See Supporting Information.
  • 35
    • 78349250733 scopus 로고    scopus 로고
    • When 1.0 and 1.5 equiv. of L -phenylalanine were employed, the yields were decreased to 17% and 50%, respectively, under the optimized conditions.
    • When 1.0 and 1.5 equiv. of L -phenylalanine were employed, the yields were decreased to 17% and 50%, respectively, under the optimized conditions.
  • 36
    • 78349237116 scopus 로고    scopus 로고
    • It is assumed that the nitrogen-oxygen interchange through the rubber of the balloon could occur to prevent the catalytic activity.
    • It is assumed that the nitrogen-oxygen interchange through the rubber of the balloon could occur to prevent the catalytic activity.
  • 37
    • 78349231456 scopus 로고    scopus 로고
    • Although it is easy to remove the inorganic base from the reaction mixture by aqueous work-up, a large amount of aqueous waste containing inorganic salts is produced and it is costly for disposal. Another advantage with the use of DBU was the ease of the purification process, which avoided the elaboration of unsoluble materials frequently observed when inorganic salts were employed as base to prevent the easy isolation of product.
    • Although it is easy to remove the inorganic base from the reaction mixture by aqueous work-up, a large amount of aqueous waste containing inorganic salts is produced and it is costly for disposal. Another advantage with the use of DBU was the ease of the purification process, which avoided the elaboration of unsoluble materials frequently observed when inorganic salts were employed as base to prevent the easy isolation of product.
  • 40
    • 78349279770 scopus 로고    scopus 로고
    • Recent reports dealing with the chiral synthesis of 3-substituted qionoxalin-2-ones, see
    • Recent reports dealing with the chiral synthesis of 3-substituted qionoxalin-2-ones, see
  • 46
    • 78349231814 scopus 로고    scopus 로고
    • [1c]
    • [1c]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.