Bioorthogonal Reactions of Oxadiazinones With Strained <i>trans</i>‐Cyclooctenes
ABSTRACT We report quantitative details of addition reactions of a strained trans ‐cyclooctene with a series of oxadiazinones, analogues of the bioorthogonally fruitful tetrazines. Both experimental and computational studies of these ligations reveal their sensitivity to differing electronic character of oxadiazinone substituents. Achieving rate constants up to 9.5 L mol −1 s −1 , oxadiazinones demonstrate untapped potential for bioorthogonal applications.
Authors
- Didier A. Bilodeau
- John Paul Pezacki (ORCID: https://orcid.org/0000-0002-4233-8945)
- Jason D. Josephson (ORCID: https://orcid.org/0000-0001-7643-5797)
- Masaya Nakajima (ORCID: https://orcid.org/0000-0002-5928-500X)
- Kaitlyn Morrill
- Baha Altamimi
Institutions
- University of Ottawa (CA)
- Chiba University (JP)
Publication Details
- Journal
- Journal of Physical Organic Chemistry
- Published
- 2024-12-22
- DOI
- https://doi.org/10.1002/poc.4674
- Citations
- 1
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Natural Sciences and Engineering Research Council of Canada