@article{85dcdb97fd454606b778be91f6ec33b9,
title = "Clip to Click: Controlling Inverse Electron-Demand Diels-Alder Reactions with Macrocyclic Tetrazines",
abstract = "A universal strategy to control tetrazine reactivity in the inverse electron-demand Diels-Alder (IEDDA) reaction was developed as {"}Clip to Click{"}. Incorporating a chemical bridge into 3,6-diphenyl-1,2,4,5-tetrazine (macrocyclic tetrazine) rendered it unreactive toward trans-cyclooctene. A computational study revealed that the unreactive property of macrocyclic tetrazines is mainly due to the high distortion energy of tetrazine. We demonstrated that the cleavage ({"}Clip{"}) of the macrocyclic linker can activate the tetrazine moiety for the IEDDA reaction ({"}Click{"}).",
author = "Ira Novianti and Toshiyuki Kowada and Shin Mizukami",
note = "Funding Information: This work was supported by JSPS and MEXT KAKENHI (Nos. JP18H02102, JP19H05284, JP20K05702, and JP21H05252) and by the Takeda Science Foundation, the Nakatani Foundation, AMED-CREST (21gm1410006h0001), and the “Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials” Research Program in the “Network Joint Research Center for Materials and Devices”. We thank the Tagen Central Analytical Facility for providing NMR and MS instruments. We thank the Cyberscience Center, Tohoku University, for providing Gaussian software. We thank Dr. Toshitaka Matsui (Tohoku University) for his assistance with reaction kinetic measurements. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",
year = "2022",
month = may,
day = "6",
doi = "10.1021/acs.orglett.2c01010",
language = "English",
volume = "24",
pages = "3223--3226",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "17",
}