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芳基三氟甲磺酸酯的 1,2-双官能化:一种直接且模块化的方法,用于合成多种功能化苯胺。

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines.

机构信息

Department of Chemistry , Duke University , 124 Science Drive , Durham , North Carolina 27708 , United States.

出版信息

Org Lett. 2020 Feb 21;22(4):1670-1674. doi: 10.1021/acs.orglett.0c00320. Epub 2020 Feb 6.

Abstract

-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation of various functionalities such as amine, azide, oxygen, sulfur, halide, alkynyl, aryl, vinyl, and alkyl groups in a modular manner for the synthesis of diverse aniline skeletons.

摘要

芳基三氟甲磺酸酯的三组分反应实现了氨基的双官能化。该级联反应通过锌酸盐碱介导的反应性芳基炔中间体的去质子化形成、亲核加成和与亲电试剂的偶联进行。该策略利用了有机锌中间体的有利反应性,能够以模块化方式在各种官能团(如胺、叠氮化物、氧、硫、卤素、炔基、芳基、乙烯基和烷基)上进行安装,用于合成各种苯胺骨架。

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