Synthesis of α-Aryl Oxindoles by Friedel-Crafts Alkylation of Arenes

被引：19

作者：

Rokade, Balaji, V ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin UCD, Ctr Synth & Chem Biol CSCB, Synth & Solid State Pharmaceut Ctr SSPC, Sch Chem, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 09期

基金：

爱尔兰科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; BRONSTED ACID; ARYLATION; 3-ARYLOXINDOLES; CONSTRUCTION; CATALYSTS; ISATINS; LIGAND;

D O I：

10.1021/acs.joc.0c00370

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Aryl oxindoles are accessed from isatin via a two-step procedure involving a phospha-Brook rearrangement and a Friedel-Crafts alkylation in a one-pot procedure. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as solvent significantly extended the reaction substrate scope to include relatively less electron-rich arenes including benzene. This new alkylation method is fast and straightforward and allows for the direct introduction of the oxindole moiety onto a range of aromatic compounds including phenols. Additionally, the application of arylated products was shown in decarboxylative asymmetric allylation and protonation.

引用

页码：6172 / 6180

页数：9

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