The dual reactivity of amides fused to 2-(5-phenylisoxazol-3-yl)aniline as a directing group for the formation of urea derivatives via chemospecific cleavage of the C(═O)─C bond and C(sp)-H amination is reported here. Employing inexpensive copper as the catalyst and O in air as the oxidant, this protocol exhibited broad functional group tolerance for both the transformations. Detailed mechanistic studies and DFT calculations were performed to gain insights into a plausible mechanism for the formation of urea derivatives.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c03104 | DOI Listing |
Publication Analysis
Top Keywords
urea derivatives
12
dual reactivity
8
formation urea
8
copperii-mediated dual
4
reactivity 2-5-phenylisoxazol-3-ylaniline
4
2-5-phenylisoxazol-3-ylaniline directed
4
directed amination
4
amination oxidative
4
oxidative c═o─c
4
c═o─c cleavage
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!