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

Angewandte Chemie
Yangyang QuPierre Audebert

Abstract

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

References

Aug 30, 2001·Journal of the American Chemical Society·D L Boger, J Hong
Jul 28, 2005·Journal of the American Chemical Society·Akiyuki HamasakiDale L Boger
Oct 19, 2006·Chemical Communications : Chem Comm·Yuna KimPierre Audebert
Sep 19, 2008·Journal of the American Chemical Society·Melissa L BlackmanJoseph M Fox
Dec 5, 2008·Bioconjugate Chemistry·Neal K DevarajScott A Hilderbrand
Mar 23, 2010·Chemical Reviews·Gilles Clavier, Pierre Audebert
Sep 3, 2010·Journal of the American Chemical Society·Zhao LiYe Tao
Aug 16, 2011·Chemical Reviews·Haixiang Gao, Jean'ne M Shreeve
Sep 29, 2011·Bioconjugate Chemistry·Mark R KarverScott A Hilderbrand
Dec 14, 2011·Angewandte Chemie·Mark R KarverScott A Hilderbrand
Dec 20, 2011·Journal of the American Chemical Society·Daniel S LiuAlice Y Ting
Apr 5, 2012·Angewandte Chemie·Tilman PlassEdward A Lemke
May 31, 2012·Angewandte Chemie·Katherine S YangRalph Weissleder
Jul 13, 2012·Advanced Materials·Do Kyung HwangBernard Kippelen
May 29, 2013·Angewandte Chemie·Jonathan C T CarlsonRalph Weissleder
Jun 12, 2014·Angewandte Chemie·Labros G MeimetisRalph Weissleder
Apr 2, 2015·Journal of the American Chemical Society·Chayasith UttamapinantJason W Chin
Jul 2, 2015·Journal of the American Chemical Society·Fabian EhretNeal K Devaraj
Aug 1, 2015·Angewandte Chemie·Paresh AgarwalCarolyn R Bertozzi
Aug 12, 2016·Journal of the American Chemical Society·Haoxing WuNeal K Devaraj
Feb 24, 2017·Angewandte Chemie·David E ChavezGreg H Imler

❮ Previous
Next ❯

Citations

Apr 28, 2020·Chemistry : a European Journal·Juraj GaletaMilan Vrabel
Aug 20, 2020·Chemical Communications : Chem Comm·Enric RosAntoni Riera
Mar 12, 2021·Organic Letters·Simon D SchnellKarl Gademann
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sang-Kee ChoiEunha Kim
May 27, 2021·The Journal of Physical Chemistry. a·Xianlu CuiLili Zhao
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Clève D MboyiJean-Cyrille Hierso
Jun 24, 2021·Inorganic Chemistry·Anthony W McDonaghCaterina F Ramogida
Oct 12, 2019·Journal of the American Chemical Society·William D LambertJoseph M Fox

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cardiomyopathy

Cardiomyopathy is a disease of the heart muscle, that can lead to muscular or electrical dysfunction of the heart. It is often an irreversible disease that is associated with a poor prognosis. There are different causes and classifications of cardiomyopathies. Here are the latest discoveries pertaining to this disease.