Direct Hydrodefluorination of CF3‑Alkenes via a Mild SN2′ Process Using Rongalite as a Masked Proton Reagent

A concise and efficient hydrodefluorination process was developed for the synthesis of gem-difluoroalkenes. This reaction employs rongalite as a masked proton source and does not require any additional catalysts or reductants. Notably, trifluoromethyl alkenes having both terminal and internal double...

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Bibliographic Details
Published in:Organic letters 2023-04, Vol.25 (13), p.2294-2299
Main Authors: Chen, Xiang-Long, Yang, Dong-Sheng, Tang, Bo-Cheng, Wu, Chun-Yan, Wang, Huai-Yu, Ma, Jin-Tian, Zhuang, Shi-Yi, Yu, Zhi-Cheng, Wu, Yan-Dong, Wu, An-Xin
Format: Article
Language:English
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Summary:A concise and efficient hydrodefluorination process was developed for the synthesis of gem-difluoroalkenes. This reaction employs rongalite as a masked proton source and does not require any additional catalysts or reductants. Notably, trifluoromethyl alkenes having both terminal and internal double bonds are compatible with this process, allowing for a wider range of substrates. The successful late-stage functionalizations of pharmaceuticals and gram-scale syntheses were used to demonstrate the viability of this method.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00645