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Volumn 4, Issue 12, 2015, Pages 1386-1391

Electronically Matching C-H Alkylation Strategies for the Synthesis of α-Heteroaryl Acetic Acid Derivatives

Author keywords

C H activation; Cross coupling; Photocatalysis; Vicarious nucleophilic aromatic substitution; heteroaryl acetic acid derivatives

Indexed keywords


EID: 84955165337     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201500388     Document Type: Article
Times cited : (17)

References (72)
  • 1
    • 0005421573 scopus 로고    scopus 로고
    • 3rded., New Age, New Delhi
    • A. Kar, Medicinal Chemistry, 3rded., New Age, New Delhi, 2005, pp.450-455;
    • (2005) Medicinal Chemistry , pp. 450-455
    • Kar, A.1
  • 4
    • 84955216958 scopus 로고    scopus 로고
    • Glaxo Group Limited, Middlesex, UK), WO 2008/125600.
    • B. P. John, D. D. Kenneth, W. D. Simon (Glaxo Group Limited, Middlesex, UK), WO 2008/125600.
    • John, B.P.1    Kenneth, D.D.2    Simon, W.D.3
  • 10
    • 84955171610 scopus 로고    scopus 로고
    • For limited examples of heteroarylboron compounds in the coupling with α-haloacetates, see:
    • For limited examples of heteroarylboron compounds in the coupling with α-haloacetates, see:
  • 13
    • 84955210767 scopus 로고    scopus 로고
    • For reactions of arylboron compounds and α-haloacetates, see:
    • For reactions of arylboron compounds and α-haloacetates, see:
  • 20
    • 84955208657 scopus 로고    scopus 로고
    • For recent reviews of C-H functionalization reactions of heteroarenes, see:
    • For recent reviews of C-H functionalization reactions of heteroarenes, see:
  • 26
    • 84955213676 scopus 로고    scopus 로고
    • For reviews on catalytic C-H alkylation reactions, see:
    • For reviews on catalytic C-H alkylation reactions, see:
  • 29
    • 81355154663 scopus 로고    scopus 로고
    • X. Hu, Chem. Sci. 2011, 2, 1867-1886.
    • (2011) Chem. Sci. , vol.2 , pp. 1867-1886
    • Hu, X.1
  • 30
    • 84955205807 scopus 로고    scopus 로고
    • For the use of α-haloaceates in directing group-assisted C-H functionalization reactions, see:
    • For the use of α-haloaceates in directing group-assisted C-H functionalization reactions, see:
  • 36
    • 84955185004 scopus 로고    scopus 로고
    • For reviews on the vicarious nucleophilic aromatic substitution reactions, see:
    • For reviews on the vicarious nucleophilic aromatic substitution reactions, see:
  • 39
    • 84955204299 scopus 로고    scopus 로고
    • For recent examples of Pd-catalyzed alkylation of heteroarenes, see:
    • For recent examples of Pd-catalyzed alkylation of heteroarenes, see:
  • 45
    • 84955187679 scopus 로고    scopus 로고
    • For recent reviews on visible-light-induced photocatalysis, see:
    • For recent reviews on visible-light-induced photocatalysis, see:
  • 56
    • 65649124191 scopus 로고    scopus 로고
    • For a single example of the use of ethyl chloroacetate in a reaction with a fused nitroimidazole, imidazo[1,2-a]pyridine, see
    • For a single example of the use of ethyl chloroacetate in a reaction with a fused nitroimidazole, imidazo[1, 2-a]pyridine, see: M. Rahimizadeh, M. Pordel, M. Bakavoli, H. Eshghi, A. Shiri, Mendeleev Commun. 2009, 19, 161-162.
    • (2009) Mendeleev Commun. , vol.19 , pp. 161-162
    • Rahimizadeh, M.1    Pordel, M.2    Bakavoli, M.3    Eshghi, H.4    Shiri, A.5
  • 57
    • 84955191287 scopus 로고    scopus 로고
    • A VNS reaction of nitrothiophene and ethyl chloroacetate was reported (63% yield)., F. Hoffmann-La Roche AG, Basle, Switzerland), WO 2002/002567.
    • A VNS reaction of nitrothiophene and ethyl chloroacetate was reported (63% yield). A. L. Gill, W. Harris (F. Hoffmann-La Roche AG, Basle, Switzerland), WO 2002/002567.
    • Gill, A.L.1    Harris, W.2
  • 59
    • 84901255512 scopus 로고    scopus 로고
    • Heating a solution of triphenylphosphine and ethyl chloroacetate at 110°C for 72h was required to afford the corresponding triphenylphosphorane.
    • Heating a solution of triphenylphosphine and ethyl chloroacetate at 110°C for 72h was required to afford the corresponding triphenylphosphorane. C. Pieri, D. Borselli, C. DiGiorgio, M. DeMéo, J.-M. Bolla, N. Vidal, S. Combes, J. M. Brunel, J. Med. Chem. 2014, 57, 4263-4272.
    • (2014) J. Med. Chem. , vol.57 , pp. 4263-4272
    • Pieri, C.1    Borselli, D.2    DiGiorgio, C.3    DeMéo, M.4    Bolla, J.-M.5    Vidal, N.6    Combes, S.7    Brunel, J.M.8
  • 60
    • 84955192083 scopus 로고    scopus 로고
    • 3 resulted in the formation of a trace amount of 4 (<5%).
    • 3 resulted in the formation of a trace amount of 4 (<5%).
  • 62
    • 84955170721 scopus 로고    scopus 로고
    • For recent examples, see:
    • For recent examples, see:
  • 69
    • 84918793037 scopus 로고    scopus 로고
    • Recently, the Stephenson group performed an elegant mechanistic study on the Ir-catalyzed C2 alkylation reaction of 3-methylindole.
    • Recently, the Stephenson group performed an elegant mechanistic study on the Ir-catalyzed C2 alkylation reaction of 3-methylindole. J. J. Devery III, J. J. Douglas, J. D. Nguyen, K. P. Cole, R. A. Flowers II, C. R. J. Stephenson, Chem. Sci. 2015, 6, 537-541.
    • (2015) Chem. Sci. , vol.6 , pp. 537-541
    • Devery, J.J.1    Douglas, J.J.2    Nguyen, J.D.3    Cole, K.P.4    Flowers, R.A.5    Stephenson, C.R.J.6
  • 70
    • 85027931643 scopus 로고    scopus 로고
    • For the photocatalytic cycle involving oxidative quenching pathways, see
    • For the photocatalytic cycle involving oxidative quenching pathways, see: J. Jung, E. Kim, Y. You, E. J. Cho, Adv. Synth. Catal. 2014, 356, 2741-2748.
    • (2014) Adv. Synth. Catal. , vol.356 , pp. 2741-2748
    • Jung, J.1    Kim, E.2    You, Y.3    Cho, E.J.4
  • 71
    • 84955189693 scopus 로고    scopus 로고
    • 4 and DMF, the corresponding over-alkylation product, diethyl 2-(5-acetyl-1-methyl-1H-pyrrol-2-yl)succinate was isolated in 21% yield.
    • 4 and DMF, the corresponding over-alkylation product, diethyl 2-(5-acetyl-1-methyl-1H-pyrrol-2-yl)succinate was isolated in 21% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.