通过可见光诱导 Pd 催化 Heck 型烷基化反应来获取 α-酯腙的幻觉异构体。
Accessing Illusive Isomers of α-Ester Hydrazones via Visible-Light-Induced Pd-Catalyzed Heck-Type Alkylation.
机构信息
Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080-3021, United States.
出版信息
Org Lett. 2022 Jun 17;24(23):4176-4181. doi: 10.1021/acs.orglett.2c01409. Epub 2022 Jun 2.
Abstract
A visible-light-induced Pd-catalyzed stereoselective synthesis of alkylated ester hydrazones has been developed. This method operates via generation of a nucleophilic carbon-centered radical from alkyl bromide, iodide, or redox-active ester, followed by its addition to hydrazone, and a subsequent desaturation by palladium. The majority of products have configuration, which are inaccessible by conventional condensation methods. In addition, a sequential C,N-alkylation protocol has been developed: a reaction between 1,3-dihalides and glyoxylate-derived hydrazone, delivering tetrahydropyridazines.
摘要
可见光诱导的 Pd 催化的立体选择性合成烷基化酯腙已经被开发出来。该方法通过从烷基溴化物、碘化物或氧化还原活性酯生成亲核碳中心自由基，然后将其加成到腙上，并通过钯进行随后的去饱和来进行操作。大多数产物具有构型，这是传统缩合方法无法获得的。此外，还开发了一种顺序 C，N-烷基化方案：1,3-二卤化物和乙二醛衍生的腙之间的反应，生成四氢吡啶嗪。
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