Triple Catalysis for the Tandem Transformation of Cyclopropyl Ketones to SCF<sub>3</sub>-Substituted Dihydrofurans
In this study, we have developed an effective and general strategy for synthesizing various 4-[(trifluoromethyl)thio]-2,3-dihydrofuran derivatives with high regioselectivity from easily prepared cyclopropyl ketone under mild reaction conditions. By the combination of photoredox, copper, and Lewis acid catalysis into a triple catalytic system, this methodology facilitates the selective cleavage of the carbon-carbon bonds and the formation of new carbon-oxygen and carbon-sulfur bonds. In addition, to enhance the synthetic feasibility of this protocol, we demonstrate its broad applicability across a wide range of substrates and its scalability for large-scale synthesis.
Authors
- Sourabh Biswas (ORCID: https://orcid.org/0000-0001-6187-8106)
- Sumit Garai (ORCID: https://orcid.org/0000-0002-9272-3681)
- Devarajulu Sureshkumar (ORCID: https://orcid.org/0000-0002-6985-3496)
- Koustav Pal
- Manasi Mallick
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c02959
- Citations
- 4
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.83
Funders
- Council of Scientific and Industrial Research, India
- University Grants Commission
- Indian Institute of Science Education and Research Kolkata
- Science and Engineering Research Board