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钯催化乙烯基苯并噁唑烷酮与芳基的脱羧偶联合成顺式-5,5a,6,10b-四氢茚并[2,1-b]吲哚

Synthesis of cis-5,5a,6,10b-Tetrahydroindeno[2,1-b]indoles through Palladium-Catalyzed Decarboxylative Coupling of Vinyl Benzoxazinanones with Arynes.

机构信息

The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.

Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University , Shenzhen 518055, China.

出版信息

Org Lett. 2018 Mar 2;20(5):1417-1420. doi: 10.1021/acs.orglett.8b00192. Epub 2018 Feb 20.

DOI:10.1021/acs.orglett.8b00192
PMID:29461841
Abstract

A novel palladium-catalyzed decarboxylative coupling reaction of vinyl benzoxazinanones with arynes which may feature an intramolecular nucleophilic attack of an amino group at the central carbon of π-allylpalladium intermediate has been developed. The cis-5,5a,6,10b-tetrahydroindeno[2,1-b]indoles were generated in moderate to good yields. One key to the success of the present reaction was to achieve comparable rates for the palladium-catalyzed decarboxylation and aryne formation steps.

摘要

一种新型钯催化的乙烯基苯并噁唑烷酮与芳炔的脱羧偶联反应,可能具有氨基在π-烯丙基钯中间体的中心碳原子上的分子内亲核进攻的特征。顺式-5,5a,6,10b-四氢茚并[2,1-b]吲哚以中等至良好的收率生成。本反应成功的关键之一是实现钯催化脱羧和芳炔形成步骤的可比速率。

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