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

Qu, Y; Sauvage, F-X; Clavier, G; Miomandre, F; Audebert, P, Angewandte Chemie-International Edition, 2018, 57, 12057-12061.

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 13C labeling of DCM, and is also presented and discussed as well as the photophysical and electrochemical properties.

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Publication

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Paru le 10 septembre 2018

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DOI: 10.1002/anie.201804878