Electron Donor–Acceptor Complex-Enabled Autoinductive Conversion of Acylnitromethanes to Acylnitrile Oxides in a Photochemical Machetti–De Sarlo Reaction: Synthesis of 5-Substituted 3-Acylisoxazoles
A photochemical Machetti-De Sarlo reaction has been developed for preparing 5-substituted 3-acylisoxazoles from acylnitromethanes and terminal alkynes. This photochemical protocol utilizes an innovative electron donor-acceptor complex, generated <i>in situ</i> from acylnitromethanes, catalytic LiO<sup><i>t</i></sup>Bu, and 1,1,1,3,3,3-hexafluoro-2-propanol, as a photosensitizer to promote rapid conversion with a broad substrate scope in up to 80% efficiency. A sigmoidal autoinductive kinetic profile is revealed, demonstrating the novel and unique dual catalysis in the first photochemical approach of this reaction.
Authors
- Nattawadee Chaisan
- Jumreang Tummatorn (ORCID: https://orcid.org/0000-0002-1662-151X)
- Charnsak Thongsornkleeb (ORCID: https://orcid.org/0000-0003-2653-5137)
- Piyaporn Arunkirirote
- Pornteera Suwalak
- Somsak Ruchirawat
Institutions
- Chulabhorn Graduate Institute (TH)
- Chulabhorn Research Institute (TH)
- Office of the Assistant Secretary for Health (US)
- Office of the Higher Education Commission (TH)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-30
- DOI
- https://doi.org/10.1021/acs.orglett.4c02708
- Citations
- 14
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- Chulabhorn Royal Academy
- National Research Council of Thailand
- Chulabhorn Research Institute
- Ministry of Higher Education, Science, Research and Innovation, Thailand
- Thailand Science Research and Innovation
- Chulabhorn Graduate Institute, Chulabhorn Royal Academy