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Volumn 10, Issue 16, 2008, Pages 3559-3562

A new H2O2/acid anhydride system for the iodoarene-catalyzed C-C bond-forming reactions of phenols

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; HYDROGEN PEROXIDE; IODINATED HYDROCARBON; KETONE; PEROXIDE; PHENOL DERIVATIVE; SPIRO COMPOUND; TRIFLUOROACETIC ACID; TRIFLUOROETHANOL;

EID: 54049111473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801321f     Document Type: Article
Times cited : (145)

References (40)
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    • Other examples: (a) Yamamoto, Y.; Kawano, Y.; Toy, P. H.; Togo, H. Tetrahedron 2007, 63, 4680.
    • Other examples: (a) Yamamoto, Y.; Kawano, Y.; Toy, P. H.; Togo, H. Tetrahedron 2007, 63, 4680.
  • 9
    • 0001213492 scopus 로고    scopus 로고
    • For recent reviews of hypervalent iodine chemistry, see: a
    • For recent reviews of hypervalent iodine chemistry, see: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1996) Chem. Rev , vol.96 , pp. 1123
    • Stang, P.J.1    Zhdankin, V.V.2
  • 15
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    • Wirth, T, Ed, Springer-Verlag: Berlin, Heidelberg
    • (g) Hvpervalent Iodine Chemistry; Wirth, T., Ed,; Springer-Verlag: Berlin, Heidelberg, 2003.
    • (2003) Hvpervalent Iodine Chemistry
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    • Recent reports: (a) Marco-Contelles, J.; Carreiras, M. C.; Rodriguez, C.; Villarroya, M.; Garcia, A. G. Chem. Rev. 2006, 106, 116.
  • 25
    • 2342485821 scopus 로고    scopus 로고
    • For synthetic studies using hypervalent iodine reagents, see ref 6a,b and others: (a) Kodama, S, Takita, H, Kajimoto, T, Nishide, K, Node, M Tetrahedron 2004, 60, 4901
    • For synthetic studies using hypervalent iodine reagents, see ref 6a,b and others: (a) Kodama, S.; Takita, H.; Kajimoto, T.; Nishide, K.; Node, M Tetrahedron 2004, 60, 4901.
  • 28
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    • Formation of reactive phenoxenium ions was proposed in iodine(HI)-induced oxidations of phenols: (a) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
    • Formation of reactive phenoxenium ions was proposed in iodine(HI)-induced oxidations of phenols: (a) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
  • 31
    • 61349163455 scopus 로고    scopus 로고
    • 2 using trifluoroperacetic acid: (a) Yagupolskii, L. M.; Maketina, I. I.; Kondratenko, N. V.; Orda, V. V. Synthesis 1978, 835.
    • 2 using trifluoroperacetic acid: (a) Yagupolskii, L. M.; Maketina, I. I.; Kondratenko, N. V.; Orda, V. V. Synthesis 1978, 835.
  • 34
  • 36
    • 61349103532 scopus 로고    scopus 로고
    • General Experimental Procedure. To a stirred solution of urea·H2O2 (94 mg, 1 mmol) in TFE (5 mL) was added TFAA (0.60 mL, 4 mmol) at -40 °C. After 30 min, 4-fluoroiodobenzene 1b (11.1 rag, 0.05 mmol) and phenol 2a (191.7 mg, 0.5 mmol) were quickly added, and the temperature was allowed to warm slowly toward -10 °C. After addition of AcOEt, the reaction mixture was quenched with aqueous satd sodium thiosulfate and washed with satd NaHCO3 aqueous. The aqueous layer was extracted using AcOEt, and the combined organic phase was washed with brine and then dried over anhydrous Na2SO4 After evaporation of the solvent, the residue was purified by column chromatography on silica gel (eluent: hexane/AcOEt, 1/1, ca. 300 mL) to give 3a in 76% yield (144.6 mg, 0.38 mmol) as colorless crystals. The spectroscopic data, 1H and 13C NMR, IR) and mp were consistent with the values fro
    • 6a
  • 38
    • 61349155936 scopus 로고    scopus 로고
    • In the control experiment, 4-FC6H4I(OCOCF 3)2 B was isolated in a nearly quantitative yield after evaporation of TFE, although a trace amount of the μ-oxo-bridged iodine(III) dimer [4-FC6H4IOCOCF3, 2O B′ was also detected. See the Supporting Information, Chart 1
    • 2O B′ was also detected. See the Supporting Information, Chart 1.
  • 39
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    • On the iodine(IIl) species including alcohol solvents as ligands: (a) Schardt, B. C.; Hill, C. L. Inorg. Chem. 1983, 22, 1563.
    • On the iodine(IIl) species including alcohol solvents as ligands: (a) Schardt, B. C.; Hill, C. L. Inorg. Chem. 1983, 22, 1563.
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    • Silva, L. F., Jr.; Lopes, N. P. Tetrahedron Lett. 2005, 46, 6023. See also ref 5i.
    • (b) Silva, L. F., Jr.; Lopes, N. P. Tetrahedron Lett. 2005, 46, 6023. See also ref 5i.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.