Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 37, Pages 12057-12061Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804878
Keywords
bioorthogonal reactions; click chemistry; cycloadditions; metal-free synthesis; tetrazines
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Funding
- European Union's Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant [674990]
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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 (13)Clabeling of DCM, and is also presented and discussed as well as the photophysical and electrochemical properties.
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