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Direct Hydrodefluorination of CF3-Alkenes via a Mild SN2′ Process Using Rongalite as a Masked Proton Reagent
Organic Letters ( IF 5.2 ) Pub Date : 2023-03-23 , DOI: 10.1021/acs.orglett.3c00645
Xiang-Long Chen 1 , Dong-Sheng Yang 1 , Bo-Cheng Tang 2 , Chun-Yan Wu 1 , Huai-Yu Wang 1 , Jin-Tian Ma 1 , Shi-Yi Zhuang 1 , Zhi-Cheng Yu 1 , Yan-Dong Wu 1 , An-Xin Wu 1
Affiliation  

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.

中文翻译:

使用雕白粉作为掩蔽质子试剂通过温和的 SN2' 过程直接加氢脱氟 CF3-烯烃

开发了一种简洁高效的加氢脱氟工艺用于合成二氟烯烃。该反应使用雕白粉作为掩蔽质子源,不需要任何额外的催化剂或还原剂。值得注意的是,同时具有末端双键和内部双键的三氟甲基烯烃与该过程兼容,可用于更广泛的底物。成功的后期药物功能化和克级合成被用来证明这种方法的可行性。
更新日期:2023-03-23
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