Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
Org Lett. 2023 Jul 14;25(27):5073-5077. doi: 10.1021/acs.orglett.3c01764. Epub 2023 Jun 30.
A regio- and stereoselective allylation of -unsubstituted anilines has been developed that explores aryl allenes as masked allyl synthons and a combination of Mg(OTf)/HFIP as an effective proton source. The protocol is operationally simple and scalable and offers high yields of diverse -allyl anilines bearing an olefin motif with exclusive -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.
一种区域和立体选择性的未取代苯胺烯丙基化反应已经被开发出来，该反应探索了芳基丙二烯作为掩蔽的烯丙基合成子，以及 Mg(OTf)/HFIP 的组合作为有效的质子源。该方案操作简单且可扩展，并能以高收率得到具有独特 - 立体化学的各种带有烯烃基序的 - 烯丙基苯胺。该方法也适用于吲哚的区域选择性烯丙基化，并可通过使用 NIS 活化剂在三组分反应模式中进行推进。用 TfOH 改变催化体系导致丙二烯的区域选择性双官能化，遵循烯丙基化/氢芳基化级联反应。
