Journal
ORGANIC LETTERS
Volume 24, Issue 16, Pages 3009-3013Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00916
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Funding
- National Natural Science Foundation of China [22001233]
- Natural Science Foundation of Zhejiang Province [LQ20B020004]
- Zhejiang Normal University [2019ZS0602]
- Open Research Fund of Key Laboratory of the Ministry of Education for Advanced Catalysis Materials
- Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University
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In this study, we designed and synthesized a new electrophilic trifluoromethylselenolation reagent, trifluoromethyl selenoxides, which were successfully applied to metal-free C-H trifluoromethylselenolation reactions of (hetero)arenes.
The trifluoromethylselenyl group (CF3Se) has become an emerging fluorinated moiety in synthetic chemistry due to its high Hansch lipophilicity parameter and strong electron-withdrawing effect. The trifluoromethylselenolation is hampered by limited synthetic methods and related reagents. Herein, we designed and synthesized the new electrophilic trifluoromethylselenolation reagents, trifluoromethyl selenoxides, which are easy to prepare and easy-to-handle and are not moisture or air sensitive. The selenoxides are successfully applied to metal-free C-H trifluoromethylselenolation of a series of (hetero)arenes.
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