文献类型：期刊文献

英文题名：Visible-light mediated directed perfluoroalkylation of hydrazones

作者：Ji, Heng[1,2];Ni, Hui-qiong[1];Zhi, Peng[2];Xi, Zi-wei[2];Wang, Wei[3];Shi, Jian-jun[1];Shen, Yong-miao[2]

机构：[1]Anhui Univ Sci & Technol, Sch Chem Engn, Huainan, Peoples R China;[2]Shaoxing Univ, Key Lab Clean Dyeing & Finishing Technol Zhejiang, Sch Chem & Chem Engn, Shaoxing 312000, Peoples R China;[3]Yancheng Inst Technol, Sch Chem & Biol Engn, Yancheng, Peoples R China

年份：2017

卷号：15

期号：28

起止页码：6014

外文期刊名：ORGANIC & BIOMOLECULAR CHEMISTRY

收录：SCI-EXPANDED(收录号：WOS:000406094000021)、、EI(收录号：20173003969376)、Scopus(收录号：2-s2.0-85025113140)、WOS、CCR-EXPANDED(收录号：WOS:000406094000021)

基金：This work was supported by the National Natural Science Foundation of China (NSFC 21202101), the Zhejiang Provincial Natural Science Foundation (LY16B020006) and the China Postdoctoral Science Foundation (2015 M581919).

语种：英文

外文关键词：Aldehydes - Aromatic compounds - Free radicals

外文摘要：Perfluoroalkylation of N-alkylhydrazones has been achieved via visible light mediated photoredox reactions between the hydrazone and perfluoroalkyl iodide (RfI). This protocol provides a convenient and efficient access to a series of perfluoroalkylated aromatic aldehyde hydrazones which tolerates a wide range of functional groups on the aromatic ring, and allows the use different types of primary and secondary perfluoroalkyl iodides with up to eight carbon atoms. Furthermore, aliphatic aldehyde hydrazones and N-monosubstituted hydrazones which are unreactive in previously reported hydrazone perfluoroalkylation reactions now take part in the reaction under our reaction conditions to give a satisfactory yield of products. Stern-Volmer quenching studies and spin-trapping experiments indicated that these reactions proceed by free radical addition of the R-f radical to the azomethine atom followed by one electron oxidation of the hydrazyl radical and deprotonation of the diazenium cation.