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

Weisen Yang; Rongli Zhang; Feiyan Yi; Mingzhong Cai

doi:10.1021/acs.joc.7b00386

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

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

Authors

Weisen Yang^{1

2}, Rongli Zhang¹, Feiyan Yi¹, Mingzhong Cai¹

Affiliations

¹ Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University , Nanchang 330022, P. R. China.
² College of Ecology and Resources Engineering, Wuyi University , Wuyishan City 354300, P. R. China.

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

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.

Publication types

Research Support, Non-U.S. Gov't