通过 Wagner-Meerwein 重排实现邻磺酰胺键联亚烷基环丙烷的无催化剂双氨基氟化反应。
Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement.
机构信息
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
出版信息
Chem Commun (Camb). 2018 Sep 13;54(74):10503-10506. doi: 10.1039/c8cc05634j.
A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.
发展了一种无催化剂的邻磺酰胺缩烯丙基环丙烷的分子内偕二氨基氟化反应。该反应通过两个 SET 过程与 Selectfluor 进行，生成氟化环丙基甲鎓和进一步的 Wagner-Meerwein 重排，生成环丁基碳正离子，后者通过酰胺进行分子内亲核捕获，生成氟化环丁[b]吲哚衍生物。在某些情况下，还通过里特型反应形成了多环多氟化副产物。
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