37385-31-2Relevant academic research and scientific papers
Cross-Coupling Reactions of Monosubstituted Tetrazines
Hoff, Lukas V.,Schnell, Simon D.,Tomio, Andrea,Linden, Anthony,Gademann, Karl
supporting information, p. 5689 - 5692 (2021/08/16)
A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1′-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).
Metal-Free Synthetic Approach to 3-Monosubstituted Unsymmetrical 1,2,4,5-Tetrazines Useful for Bioorthogonal Reactions
Qu, Yangyang,Sauvage, Fran?ois-Xavier,Clavier, Gilles,Miomandre, Fabien,Audebert, Pierre
supporting information, p. 12057 - 12061 (2018/09/06)
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.
