Group 13 Lewis acid-mediated formation of 5-oxazolone derivatives from <i>tert</i>-butyl isocyanoacetate
<i>tert</i>-Butyl isocyanoacetate 1 reacted with B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> to give a Lewis acid-base adduct 2. GaCl<sub>3</sub> and GaI<sub>3</sub> promoted cyclization affording the N-bound Lewis acid adducts of the cyclized product 5-oxazolone derivatives 3 and 4, resulting from isocyano insertion into the ester C-O bond, with the loss of isobutylene. In contrast, the reactions with InBr<sub>3</sub> and InI<sub>3</sub> afforded the analogous adducts of 5(4<i>H</i>)-oxazolone derivatives 5 and 6, without the loss of the <i>tert</i>-butyl group. A proposed reaction mechanism is provided for these reactions of 1.
Authors
- S.Q. Ju
- Yile Wu (ORCID: https://orcid.org/0000-0002-8450-5254)
- Douglas W. Stephan (ORCID: https://orcid.org/0000-0001-8140-8355)
- He Zhou (ORCID: https://orcid.org/0000-0002-1871-9756)
- Ting Chen (ORCID: https://orcid.org/0000-0002-9252-8798)
- Xinghua Zhang
Institutions
- Ningbo University (CN)
- Ningbo University of Technology (CN)
- University of Toronto (CA)
- Ningbo University of Finance & Economics (CN)
- Shanghai Institute of Technology (CN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc02623g
- Primary Topic
- Synthesis and Reactions of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Natural Science Foundation of Ningbo