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Volumn 46, Issue 9, 2007, Pages 1423-1426

The oxorhenium(VII)-catalyzed direct condensation of phosphoric acid with an alcohol

Author keywords

Alcohols; Green chemistry; Homogeneous catalysis; Phosphoric acid monoesters; Rhenium

Indexed keywords

ALCOHOLS; CATALYSIS; COMPUTATIONAL METHODS; CONDENSATION; ESTERS; RHENIUM COMPOUNDS;

EID: 34247890173     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604333     Document Type: Article
Times cited : (43)

References (34)
  • 3
    • 0001433260 scopus 로고
    • For reviews of the synthesis of phosphoric acid esters, see: a, Eds, B. M. Trost, I. Fleming, E. Winterfeldt, Pergamon, Oxford
    • For reviews of the synthesis of phosphoric acid esters, see: a) Y. Hayakawa in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming, E. Winterfeldt), Pergamon, Oxford, 1991, pp. 601-630;
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 601-630
    • Hayakawa, Y.1
  • 9
    • 0001094491 scopus 로고    scopus 로고
    • For our recent contributions to catalytic direct condensations of carboxylic acids, see: a
    • For our recent contributions to catalytic direct condensations of carboxylic acids, see: a) K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196-4197;
    • (1996) J. Org. Chem , vol.61 , pp. 4196-4197
    • Ishihara, K.1    Ohara, S.2    Yamamoto, H.3
  • 13
    • 19544374511 scopus 로고    scopus 로고
    • We have reported that nucleophilic bases such as N-butylimidazole promote the condensation of phosphoric acid and alcohols in the presence of tributylamine. However, the catalytic activities of the nucleophilic bases were such that 2 equiv of phosphoric acid and 2 equiv of tributylamine were needed to give phosphoric acid monoesters in good yield: A. Sakakura, M. Katsukawa, K. Ishihara, Org. Lett. 2005, 7, 1999-2002
    • We have reported that nucleophilic bases such as N-butylimidazole promote the condensation of phosphoric acid and alcohols in the presence of tributylamine. However, the catalytic activities of the nucleophilic bases were such that 2 equiv of phosphoric acid and 2 equiv of tributylamine were needed to give phosphoric acid monoesters in good yield: A. Sakakura, M. Katsukawa, K. Ishihara, Org. Lett. 2005, 7, 1999-2002.
  • 14
    • 0013954717 scopus 로고    scopus 로고
    • Honjo and coworkers have reported the condensation of phosphoric acid with 2′,3′-O-isopropylidene ribonucleosides in the presence of tributylamine. In this work, a large excess of phosphoric acid (5 equiv) and tributylamine (10 equiv) was required. The reactions were conducted at reflux in DMF (b.p. 153°C), and the yields were low (38-58%). Since DMF decomposes gradually at its boiling point, the obtained crude products must be highly contaminated with impurities produced by the decomposition of DMF: M. Honjo, Y. Furukawa, K. Kobayashi, Chem. Pharm. Bull. 1966, 14, 1061-1065.
    • Honjo and coworkers have reported the condensation of phosphoric acid with 2′,3′-O-isopropylidene ribonucleosides in the presence of tributylamine. In this work, a large excess of phosphoric acid (5 equiv) and tributylamine (10 equiv) was required. The reactions were conducted at reflux in DMF (b.p. 153°C), and the yields were low (38-58%). Since DMF decomposes gradually at its boiling point, the obtained crude products must be highly contaminated with impurities produced by the decomposition of DMF: M. Honjo, Y. Furukawa, K. Kobayashi, Chem. Pharm. Bull. 1966, 14, 1061-1065.
  • 15
    • 0001087127 scopus 로고    scopus 로고
    • The esterification of monosubstituted phosphonic acids has been reported. Monosubstituted phosphonic acids are less acidic than phosphoric acid: Y. R. Dumond, R. L. Baker, J.-L. Montchamp, Org. Lett. 2000, 2, 3341-3344.
    • The esterification of monosubstituted phosphonic acids has been reported. Monosubstituted phosphonic acids are less acidic than phosphoric acid: Y. R. Dumond, R. L. Baker, J.-L. Montchamp, Org. Lett. 2000, 2, 3341-3344.
  • 16
    • 0000162949 scopus 로고    scopus 로고
    • For a review of oxorhenium(VII) complexes, see: a) C. C. Romão, RE. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197-3246;
    • For a review of oxorhenium(VII) complexes, see: a) C. C. Romão, RE. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197-3246;
  • 19
    • 14844283138 scopus 로고    scopus 로고
    • For recent studies on catalysis by oxorhenium(VII) complexes, see: a) C. Morrill, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 2842-2843;
    • For recent studies on catalysis by oxorhenium(VII) complexes, see: a) C. Morrill, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 2842-2843;
  • 24
    • 0004204702 scopus 로고    scopus 로고
    • 3rd ed, Clarendon, Oxford
    • J. Emsley, The Elements, 3rd ed., Clarendon, Oxford, 1998, pp. 172-173.
    • (1998) The Elements , pp. 172-173
    • Emsley, J.1
  • 26
    • 0037119319 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 2983-2986.
    • (2002) Chem. Int. Ed , vol.41 , pp. 2983-2986
    • Angew1
  • 28
    • 34250716411 scopus 로고    scopus 로고
    • In our previous work, 6] a 1:1 mixture of DMF and EtNO2 was used as solvent. Since phosphoric acid is not soluble in this mixture, 1 equiv of tributylamine was required to dissolve the phosphoric acid and promote the reaction
    • 2 was used as solvent. Since phosphoric acid is not soluble in this mixture, 1 equiv of tributylamine was required to dissolve the phosphoric acid and promote the reaction.
  • 29
    • 34250791226 scopus 로고    scopus 로고
    • Igepal CO-210 (purchased from Aldrich) is a mixture of isomers. A representative structure of Igepal CO-210 is shown in Table 2.
    • Igepal CO-210 (purchased from Aldrich) is a mixture of isomers. A representative structure of Igepal CO-210 is shown in Table 2.
  • 30
    • 34250735540 scopus 로고    scopus 로고
    • Acid-sensitive alcohols might be converted into the corresponding phosphoric acid monoesters in the presence of one or more equivalents of dibutylamine
    • Acid-sensitive alcohols might be converted into the corresponding phosphoric acid monoesters in the presence of one or more equivalents of dibutylamine.
  • 31
    • 0001638530 scopus 로고    scopus 로고
    • 3 and alcohols: W. A. Herrmann, W. A. Wojtczak, G. R. J. Artus, F. E. Kühn, M. R. Mattner, Inorg. Chem. 1997, 36, 465-471.
    • 3 and alcohols: W. A. Herrmann, W. A. Wojtczak, G. R. J. Artus, F. E. Kühn, M. R. Mattner, Inorg. Chem. 1997, 36, 465-471.
  • 32
    • 34250712263 scopus 로고    scopus 로고
    • 31P NMR spectroscopy.
    • 31P NMR spectroscopy.
  • 34
    • 34250738886 scopus 로고    scopus 로고
    • When the reaction was conducted in the absence of alcohols, pyrophosphoric acid (5) was produced in about 30% yield
    • When the reaction was conducted in the absence of alcohols, pyrophosphoric acid (5) was produced in about 30% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.