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Volumn 48, Issue 43, 2009, Pages 8018-8021

Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes

Author keywords

Azides; Click chemistry; Copper; Cycloaddition; Iodoalkynes; Iodotriazoles

Indexed keywords

AZIDES; CLICK CHEMISTRY; COPPER CATALYST; FUNCTIONALIZED; HIGH FIDELITY; IODOALKYNES; IODOTRIAZOLES; ORGANIC AZIDES;

EID: 70349974178     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903558     Document Type: Article
Times cited : (424)

References (33)
  • 22
    • 29744459491 scopus 로고    scopus 로고
    • Recently reported an elegant synthesis of 5-bromo-1, 2, 3-triazoles from 1-bromoalkynes, however reactions required 40 mol% CuI/CuII, elevated temperature or 16-50 h to reach completion; B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes
    • b) Kuijpers et al. Recently reported an elegant synthesis of 5-bromo-1, 2, 3-triazoles from 1-bromoalkynes, however reactions required 40 mol% CuI/CuII, elevated temperature or 16-50 h to reach completion; B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059.
    • (2005) Synlett , pp. 3059
    • Kuijpers1
  • 23
    • 70349949007 scopus 로고    scopus 로고
    • The regiochemistry of 3 was assigned by reducing the 5-iodo center to give 5-H-triazole 4. See the Supporting Information for details.
    • The regiochemistry of 3 was assigned by reducing the 5-iodo center to give 5-H-triazole 4. See the Supporting Information for details.
  • 26
    • 70349952320 scopus 로고
    • US Patent 2
    • R. V. Rice, G. D. Beal, US Patent 2, 290, 710, 1943.
    • (1943) , vol.290 , pp. 710
    • Rice, R.V.1    Beal, G.D.2
  • 27
    • 70349947215 scopus 로고    scopus 로고
    • Addition of electrophilic iodinating reagents (N-iodomorpho-line, ICl, N-iodosuccinimide, etc.) to a solution containing CuI- TTTA, the target azide and terminal alkyne rapidly gave the corresponding 1-iodoalkyne, but failed to promote the subsequent cycloaddition. This failure is likely to be a result of the disruption of the catalytically active complex, either through oxidation of the metal or displacement/destruction of the ligand.
    • Addition of electrophilic iodinating reagents (N-iodomorpho-line, ICl, N-iodosuccinimide, etc.) to a solution containing CuI- TTTA, the target azide and terminal alkyne rapidly gave the corresponding 1-iodoalkyne, but failed to promote the subsequent cycloaddition. This failure is likely to be a result of the disruption of the catalytically active complex, either through oxidation of the metal or displacement/destruction of the ligand.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.