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.

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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

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article

Triple Catalysis for the Tandem Transformation of Cyclopropyl Ketones to SCF3-Substituted Dihydrofurans

Sourabh Biswas, Sumit Garai, Devarajulu Sureshkumar, Koustav Pal et al.
4 citations
Organic Letters
Fluorine in Organic Chemistry
0.83
article

Triple Catalysis for the Tandem Transformation of Cyclopropyl Ketones to SCF3-Substituted Dihydrofurans

Sourabh Biswas, Sumit Garai, Devarajulu Sureshkumar, Koustav Pal, Manasi Mallick
article en
4 citations

Abstract

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.

Organic LettersVol. 26(39)
Indian Institute of Science Education and Research Kolkata (IN)
Council of Scientific and Industrial Research, India, University Grants Commission, Indian Institute of Science Education and Research Kolkata, Science and Engineering Research Board
Openalex Percentile: Top 31%
Fluorine in Organic Chemistry
0.83
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