N-羟基酰亚胺作为铜催化吡咯、咪唑和吲哚N-芳基化反应的有效配体。

N-hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole.

作者信息

Ma Heng-Chang, Jiang Xuan-Zhen

机构信息

Department of Chemistry, Zhejiang University, Hangzhou, China.

出版信息

J Org Chem. 2007 Nov 9;72(23):8943-6. doi: 10.1021/jo7015983. Epub 2007 Oct 13.

DOI:10.1021/jo7015983

PMID:17935350

Abstract

An experimentally simple, efficient, and inexpensive catalyst system was developed for the N-arylation of pyrroles, indoles, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying CuI as catalyst, N-hydroxysuccinimide (L1), N-hydroxymaleimide (L2), or N-hydroxyphthalimide (L3) as ligand, CH3ONa as base, and DMSO as solvent. A variety of functional groups are tolerated in the reaction, including those that are not compatible with Pd-catalyzed amidation methodology.

摘要

通过使用碘化亚铜作为催化剂、N-羟基琥珀酰亚胺（L1）、N-羟基马来酰亚胺（L2）或N-羟基邻苯二甲酰亚胺（L3）作为配体、甲醇钠作为碱以及二甲基亚砜作为溶剂，开发了一种实验上简单、高效且廉价的催化剂体系，用于吡咯、吲哚和咪唑与芳基及杂芳基碘化物、溴化物和氯化物的N-芳基化反应。该反应能耐受多种官能团，包括那些与钯催化酰胺化方法不相容的官能团。