Zhang Hui-Jun, Yang Ze-Peng, Gu Qing, You Shu-Li
School of Chemistry and Molecular Engineering , East China University of Science and Technology , 130 Meilong Road , Shanghai 200237 , China.
State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.
Org Lett. 2019 May 3;21(9):3314-3318. doi: 10.1021/acs.orglett.9b01060. Epub 2019 Apr 19.
An efficient synthesis of nitrogen-containing heterocycles via Pd-catalyzed tandem allylic alkylation and dearomatization reactions was reported. In this reaction design, heteroarenes such as pyridines, pyrazines, and quinolines serve as bis-nucleophiles by installing a benzoyl group at the C2 benzylic position. With but-2-ene-1,4-diyl dimethyl dicarbonate as the bis-electrophile, the tandem Pd-catalyzed intermolecular allylic alkylation/allylic dearomatization reaction of benzoylmethyl-substituted heteroarenes has been developed. 2,3-Dihydroindolizine, 6,7-dihydropyrrolo[1,2- a]pyrazine, and 1,2-dihydropyrrolo[1,2- a]quinolin derivatives were obtained in moderate to good yields.
报道了一种通过钯催化的串联烯丙基烷基化和去芳构化反应高效合成含氮杂环的方法。在该反应设计中，吡啶、吡嗪和喹啉等杂芳烃通过在C2苄基位置引入苯甲酰基作为双亲核试剂。以2-丁烯-1,4-二醇二碳酸二甲酯作为双亲电试剂，开发了钯催化的苯甲酰基甲基取代杂芳烃的分子间串联烯丙基烷基化/烯丙基去芳构化反应。以中等至良好的产率得到了2,3-二氢中氮茚、6,7-二氢吡咯并[1,2-a]吡嗪和1,2-二氢吡咯并[1,2-a]喹啉衍生物。
