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一种金(I)催化的末端炔烃、腈和氧原子的[2 + 2 + 1]环加成反应,生成 2,5-二取代恶唑。

A Heterogeneous Gold(I)-Catalyzed [2 + 2 + 1] Annulation of Terminal Alkynes, Nitriles, and Oxygen Atoms Leading to 2,5-Disubstituted Oxazoles.

机构信息

Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University , Nanchang 330022, P. R. China.

College of Ecology and Resources Engineering, Wuyi University , Wuyishan City 354300, P. R. China.

出版信息

J Org Chem. 2017 May 19;82(10):5204-5211. doi: 10.1021/acs.joc.7b00386. Epub 2017 May 1.

DOI:10.1021/acs.joc.7b00386
PMID:28459566
Abstract

The first heterogeneous gold(I)-catalyzed [2 + 2 + 1] annulation of terminal alkynes, nitriles, and oxygen atoms has been achieved by using an MCM-41-immobilized phosphine-gold(I) complex as catalyst and 8-methylquinoline N-oxide as oxidant under mild conditions, yielding a variety of 2,5-disubstituted oxazoles in good to excellent yields with broad substrate scope. The new heterogeneous gold(I) catalyst can easily be recovered by simple filtration of the reaction solution and recycled for at least eight times without significant loss of activity.

摘要

首例末端炔烃、腈和氧原子的异相金(I)催化[2+2+1]环加成反应,在温和条件下,使用负载于 MCM-41 上的膦-金(I)配合物作为催化剂,8-甲基喹啉 N-氧化物作为氧化剂,以良好至优异的收率得到了多种 2,5-二取代恶唑,底物适用范围广泛。新型异相金(I)催化剂可通过简单过滤反应溶液轻易回收,并至少重复使用 8 次而无明显活性损失。

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