Pd-Catalyzed Functionalization of Aryl Amines on a Soluble Polymer Support,Synlett

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Pd-Catalyzed Functionalization of Aryl Amines on a Soluble Polymer Support
Synlett ( IF 1.7 ) Pub Date : 2020-09-03 , DOI: 10.1055/s-0040-1707261
M. Manuel B. Marques ₁ , A. Sofia Santos

Affiliation

Abstract

Herein we report the use of a soluble polymer support PEG-2000 on Pd-catalyzed reactions to improve the functionalization of aromatic amines and the synthesis of N-heterocycles. Compatibility of metal-catalyzed reactions for assembling privileged structures such as functionalized anilines were studied. PEG-supported anilines were found to be suitable substrates for Pd-catalyzed N-arylation, Sonogashira and Heck reactions. PEGylated substrates were prepared in yields up to 94%. This work consists on a proof of concept on the use of PEGylated anilines on Pd-catalyzed cross-coupling reactions. Indole core was attained in 82% and 62% yields, via two different routes.

Publication History

Received: 21 May 2020

Accepted after revision: 28 July 2020

Publication Date:
03 September 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

Pd催化的可溶性聚合物载体上的芳胺功能化

摘要

本文中我们报道了在Pd催化的反应中使用可溶性聚合物载体PEG-2000来改善芳族胺的功能化和N杂环的合成。研究了金属催化反应用于组装特殊结构（如功能化苯胺）的相容性。发现PEG负载的苯胺是Pd催化的N-芳基化，Sonogashira和Heck反应的合适底物。制备聚乙二醇化底物的产率高达94％。这项工作基于在Pd催化的交叉偶联反应中使用PEG化苯胺的概念验证。通过两种不同的途径，吲哚核的收率分别为82％和62％。