Journal
ORGANIC LETTERS
Volume 24, Issue 1, Pages 181-185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03813
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Funding
- National Natural Science Foundation of China [21776138, 22078161, 22108124, 52103217]
- Fundamental Research Funds for the Central Universities [30920021124, 30918011314]
- Natural Science Foundation of Jiangsu [BK20180476]
- Postdoctoral Science Foundation [2019M661848]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
- Center for Advanced Materials and Technology in Nanjing University of Science and Technology
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A method for electrophilic (fluoroalkyl) sulfenylation of nucleophiles through the collaborative use of CTAB and squaric acid to promote deoxygenation of sulfonyl derivatives is reported. Mechanistic studies show that squaric acid significantly reduces the energy barrier in the first step of deoxygenation. This novel method allows for the reduction of a wide range of functionalized sulfonyl chlorides and sulfonic anhydrides and demonstrates a high tolerance to various functional groups.
A method for electrophilic (fluoroalkyl) sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barrier in the first step of deoxygenation. The mild deoxygenation process enables the reduction of a wide range of functionalized sulfonyl chlorides as well as sulfonic anhydrides. The novel method represents an operationally simple protocol using readily available reagents and exhibits broad functional group tolerance.
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