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Volumn , Issue 43, 2005, Pages 5456-5458

Synthesis of phosphorus esters by transesterification mediated by N-heterocyclic carbenes (NHCs)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE;

EID: 28044466193     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b509783e     Document Type: Article
Times cited : (49)

References (49)
  • 3
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    • The phosphorate esters attached to macrocyclic scaffolds in metal complexes have been used as anion sensors. For a recent example see: O. Molt, D. Rubeling and T. Schrader, J. Am. Chem. Soc., 2003, 125, 12086-12087;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12086-12087
    • Molt, O.1    Rubeling, D.2    Schrader, T.3
  • 28
  • 32
    • 11444262868 scopus 로고    scopus 로고
    • For NHC catalyzed cyclotrimerization of isocyanates see: H. A. Duong, M. J. Cross and J. Louie, Org. Lett., 2004, 6, 4679-4681.
    • (2004) Org. Lett. , vol.6 , pp. 4679-4681
    • Duong, H.A.1    Cross, M.J.2    Louie, J.3
  • 36
    • 20544443754 scopus 로고    scopus 로고
    • For NHC catalyzed amidation of unactivated esters with amino alcohols see: M. Movassaghi and M. A. Schmidt, Org. Lett., 2005, 7, 2453-2456.
    • (2005) Org. Lett. , vol.7 , pp. 2453-2456
    • Movassaghi, M.1    Schmidt, M.A.2
  • 38
    • 15244343088 scopus 로고    scopus 로고
    • For conversion of α,β-unsaturated aldehydes into saturated esters via an umpolung reaction catalyzed by NHCs see: A. Chan and K. A. Scheidt, Org. Lett., 2005, 7, 905-908.
    • (2005) Org. Lett. , vol.7 , pp. 905-908
    • Chan, A.1    Scheidt, K.A.2
  • 39
    • 24044495219 scopus 로고    scopus 로고
    • For one-step assembly of functionalized γ-butyrolactones from benzoins or benzaldehydes via an NHC-mediated tandem reaction see: W. Ye, G. Cai, Z. Zhuang, X. Jia and H. Zhai, Org. Lett., 2005, 7, 3769-3771.
    • (2005) Org. Lett. , vol.7 , pp. 3769-3771
    • Ye, W.1    Cai, G.2    Zhuang, Z.3    Jia, X.4    Zhai, H.5
  • 40
    • 28044447855 scopus 로고    scopus 로고
    • note
    • Free carbenes, IAd and I'Bu are now commercially available from Strem Chemicals, Inc.
  • 42
    • 28044455236 scopus 로고    scopus 로고
    • note
    • No product formation was observed on increasing the catalyst loading to 10 mol% for IPr and IMes.
  • 43
    • 0001595852 scopus 로고
    • J. Otera, Chem. Rev., 1993, 93, 1449-1470.
    • (1993) Chem. Rev. , vol.93 , pp. 1449-1470
    • Otera, J.1
  • 44
    • 28044468865 scopus 로고    scopus 로고
    • note
    • On the suggestion of a reviewer, we wish to report a limitation of this protocol. The NHCs are not compatible with acidic alcohols hence the reaction fails to proceed when phenols, trifluoroethanol or binol are used. These alcohols deactivate the carbene by protonating it. We thank the reviewer for his suggestion.
  • 45
    • 28044445103 scopus 로고    scopus 로고
    • note
    • Imidazolium salts of ICy, IAd and I'Bu are now available commercially from Ryan, Strem and Acros Chemicals.
  • 46
    • 0002893825 scopus 로고    scopus 로고
    • Macmillan Reference USA, Simon and Schuster Macmillan, New York
    • Macmillan Encyclopedia of Chemistry, ed. C. A. Bunton and J. J. Lagowski, Macmillan Reference USA, Simon and Schuster Macmillan, New York, 1997, vol. 1, pp. 343-346.
    • (1997) Macmillan Encyclopedia of Chemistry , vol.1 , pp. 343-346
    • Bunton, C.A.1    Lagowski, J.J.2
  • 49
    • 28044448942 scopus 로고    scopus 로고
    • note
    • EDPP and DMMP are used as VX-model compounds in studies relating to the nerve agents (see reference 31).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.