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Volumn 129, Issue 42, 2007, Pages 12705-12712

Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: A mechanistic report

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE IONS; CYCLOADDITION REACTION; ELECTRONIC SUBSTITUENT PARAMETERS; POLYBENZIMIDAZOLE LIGANDS;

EID: 35548939058     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072679d     Document Type: Article
Times cited : (377)

References (28)
  • 2
    • 35548988411 scopus 로고    scopus 로고
    • In our original article ref 1, we noted a weak inhibitory property of benzyl azide. We have subsequently found that commercial benzyl azide frequently contains an unidentified trace impurity that either inhibits the CuAAC reaction or poisons the copper catalyst. No inhibitory effect was observed when carefully distilled benzyl azide was employed, and therefore our prior report is in error in this respect. Such distilled material was used in all experiments described in these articles
    • In our original article (ref 1), we noted a weak inhibitory property of benzyl azide. We have subsequently found that commercial benzyl azide frequently contains an unidentified trace impurity that either inhibits the CuAAC reaction or poisons the copper catalyst. No inhibitory effect was observed when carefully distilled benzyl azide was employed, and therefore our prior report is in error in this respect. Such distilled material was used in all experiments described in these articles.
  • 6
    • 35548976637 scopus 로고    scopus 로고
    • We have observed that certain minor products of the photochemical decomposition of aromatic azides in DMSO act as potent accelerating ligands for CuAAC reactions of other aromatic azides, increasing rates by several orders of magnitude and producing unprecedented amounts of 1,5-triazoles for a copper-mediated process. These phenomena are currently being investigated and will be described in detail elsewhere. The catalytic photoproducts do not form in the presence of tert-butanol
    • We have observed that certain minor products of the photochemical decomposition of aromatic azides in DMSO act as potent accelerating ligands for CuAAC reactions of other aromatic azides, increasing rates by several orders of magnitude and producing unprecedented amounts of 1,5-triazoles for a copper-mediated process. These phenomena are currently being investigated and will be described in detail elsewhere. The catalytic photoproducts do not form in the presence of tert-butanol.
  • 8
    • 34250883966 scopus 로고    scopus 로고
    • An example of a Cu·C(triazole) intermediate obtained from a CuAAC reaction has been recently characterized by X-ray crystallography: Nolte, C, Mayer, P, Straub, B. F. Angew. Chem, Int. Ed. 2007, 46, 2101-2103
    • An example of a Cu·C(triazole) intermediate obtained from a CuAAC reaction has been recently characterized by X-ray crystallography: Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem., Int. Ed. 2007, 46, 2101-2103.
  • 27
    • 0035805365 scopus 로고    scopus 로고
    • 1A) in our parlance, with the pendant carboxylate arm serving a coordinating role: Su, C.-Y.; Yang, X.-P.; Kang, B.-S.; Mak, T. C. W. Angew. Chem., Int. Ed. 2001, 40, 1725-1728.
    • 1A) in our parlance, with the pendant carboxylate arm serving a coordinating role: Su, C.-Y.; Yang, X.-P.; Kang, B.-S.; Mak, T. C. W. Angew. Chem., Int. Ed. 2001, 40, 1725-1728.
  • 28
    • 1042265088 scopus 로고    scopus 로고
    • A similar situation of interconverting catalysts giving rise to unusual rate profiles was sorted out nicely in Nielsen, L. P. C, Stevenson, C. P, Blackmond, D. G, Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362
    • A similar situation of interconverting catalysts giving rise to unusual rate profiles was sorted out nicely in Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.