Regio- and Stereoselective Allylation of Anilines with Aryl Allenes in Hexafluoroisopropanol Solvent

被引：10

作者：

Ghosh, Suman ^{[1
]}

Saha, Shib Nath ^{[1
]}

Baidya, Mahiuddin ^{[1
]}

机构：

[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 27期

关键词：

CATALYZED ALLYLATION; ALLYLIC ALCOHOLS; HYDROAMINATION; ALKYNES; LEWIS;

D O I：

10.1021/acs.orglett.3c01764

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio- and stereoselective allylation of N-unsubstituted anilines has been developed that explores aryl allenes as masked allyl synthons and a combination of Mg(OTf)(2)/HFIP as an effective proton source. The protocol is operationally simple and scalable and offers high yields of diverse p-allyl anilines bearing an olefin motif with exclusive E-geometry. The methodology was also suitable for the regioselective allylation of indole and can be advanced in a three-component reaction mode using NIS activator. The alteration of the catalytic system with TfOH resulted in the regioselective difunctionalization of allenes, which follows an allylation/hydroarylation cascade.

引用

页码：5073 / 5077

页数：5

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