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Volumn 13, Issue 10, 2011, Pages 2714-2717

Nucleophilic deoxyfluorination of catechols

Author keywords

[No Author keywords available]

Indexed keywords

CATECHIN; CATECHOL DERIVATIVE; DOPAMINE; FLUORINATED HYDROCARBON;

EID: 79956081214     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200808q     Document Type: Article
Times cited : (35)

References (45)
  • 10
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    • Recent examples using diaryliodonium salts, see
    • Recent examples using diaryliodonium salts, see: Chun, J.-H.; Lu, S.; Lee, Y.-S.; Pike, V. W. J. Org. Chem. 2010, 75, 3332
    • (2010) J. Org. Chem. , vol.75 , pp. 3332
    • Chun, J.-H.1    Lu, S.2    Lee, Y.-S.3    Pike, V.W.4
  • 28
    • 79956138862 scopus 로고    scopus 로고
    • A contrasing experiments in our hands using cationic fluorine reagents, such as Selectfluor (1.0 equiv), (14a) for a catechol 1a at ambient temperature for 20 min resulted in forming the ortho -quinone 2a in 85% NMR yield without obtaining any fluoronated products.
    • A contrasing experiments in our hands using cationic fluorine reagents, such as Selectfluor (1.0 equiv), (14a) for a catechol 1a at ambient temperature for 20 min resulted in forming the ortho -quinone 2a in 85% NMR yield without obtaining any fluoronated products.
  • 32
    • 0035929389 scopus 로고    scopus 로고
    • Fluorination reactions of α-diketones and α-ketoacids using either Deoxofluor or DAST were reported, see
    • Fluorination reactions of α-diketones and α-ketoacids using either Deoxofluor or DAST were reported, see: Singh, R. P.; Majumder, U.; Shreeve, J. M. J. Org. Chem. 2001, 66, 6263
    • (2001) J. Org. Chem. , vol.66 , pp. 6263
    • Singh, R.P.1    Majumder, U.2    Shreeve, J.M.3
  • 34
    • 0009751387 scopus 로고    scopus 로고
    • A few examples of the cationic fluoronation of symmetric 4-alkylphenols were reported to give 4-alkyl-6,6-difluorocyclohexa-2,4-dienones, see
    • A few examples of the cationic fluoronation of symmetric 4-alkylphenols were reported to give 4-alkyl-6,6-difluorocyclohexa-2,4-dienones, see: Stavber, S.; Zupan, M. Synlett 1996, 693
    • (1996) Synlett , pp. 693
    • Stavber, S.1    Zupan, M.2
  • 35
    • 79956080371 scopus 로고    scopus 로고
    • DBU enhances the aromatization of the initial reduction products, 6,6-difluorocyclohexa-2,4-dienols.
    • DBU enhances the aromatization of the initial reduction products, 6,6-difluorocyclohexa-2,4-dienols.
  • 40
    • 79956085242 scopus 로고    scopus 로고
    • 2 (23c) smoothly proceeded in various organic solvents; however, they were less effective for the one-pot deoxyfluorination. The oxidation by Fetizon reagent (23d) was slow at room temperature, while the ortho -quinones gradually decomposed.
    • 2 (23c) smoothly proceeded in various organic solvents; however, they were less effective for the one-pot deoxyfluorination. The oxidation by Fetizon reagent (23d) was slow at room temperature, while the ortho -quinones gradually decomposed.
  • 41
    • 0035793265 scopus 로고    scopus 로고
    • MgO was used in combination with the hypervalent iodine reagents to scavenge the generated acetic acid, see
    • MgO was used in combination with the hypervalent iodine reagents to scavenge the generated acetic acid, see: Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 598
    • Espino, C.G.1    Du Bois, J.2
  • 43
    • 67649947129 scopus 로고    scopus 로고
    • Boric acid is also useful for the chemoselective, in situ protection of the catechol moiety of catechins, see
    • Boric acid is also useful for the chemoselective, in situ protection of the catechol moiety of catechins, see: Aihara, Y.; Yoshida, A.; Furuta, T.; Wakimoto, T.; Akizawa, T.; Konishi, M.; Kan, T. Bioorg. Med. Chem. Lett. 2009, 19, 4171
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 4171
    • Aihara, Y.1    Yoshida, A.2    Furuta, T.3    Wakimoto, T.4    Akizawa, T.5    Konishi, M.6    Kan, T.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.