Metal‐Free Synthetic Approach to 3‐Monosubstituted Unsymmetrical 1,2,4,5‐Tetrazines Useful for Bioorthogonal Reactions

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  • Yangyang Qu
    PPSM- CNRS- ENS Paris-Saclay 61 Avenue Président Wilson 94235 Cachan France
  • François‐Xavier Sauvage
    PPSM- CNRS- ENS Paris-Saclay 61 Avenue Président Wilson 94235 Cachan France
  • Gilles Clavier
    PPSM- CNRS- ENS Paris-Saclay 61 Avenue Président Wilson 94235 Cachan France
  • Fabien Miomandre
    PPSM- CNRS- ENS Paris-Saclay 61 Avenue Président Wilson 94235 Cachan France
  • Pierre Audebert
    PPSM- CNRS- ENS Paris-Saclay 61 Avenue Président Wilson 94235 Cachan France

書誌事項

公開日
2018-08-13
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201804878
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>A facile, efficient and metal‐free synthetic approach to 3‐monosubstituted unsymmetrical 1,2,4,5‐tetrazines is presented. Dichloromethane (DCM) is for the first time recognized as a novel reagent in the synthetic chemistry of tetrazines. Using this novel approach 11 3‐aryl/alkyl 1,2,4,5‐tetrazines were prepared in excellent yields (up to 75 %). The mechanism of this new reaction, including the role of DCM in the tetrazine ring formation, has been investigated by <jats:sup>13</jats:sup>C labeling of DCM, and is also presented and discussed as well as the photophysical and electrochemical properties.</jats:p>

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