Rhodium(iii)-catalysed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids: synthesis of benzofuran-2(3H)-ones

Jin-Long Pan; Tuan-Qing Liu; Chao Chen; Quan-Zhe Li; Wei Jiang; Tong-Mei Ding; Zhi-Qiang Yan; Guo-Dong Zhu

doi:10.1039/c9ob01553a

Rhodium(iii)-catalysed cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids: synthesis of benzofuran-2(3H)-ones

Org Biomol Chem. 2019 Sep 25;17(37):8589-8600. doi: 10.1039/c9ob01553a.

Authors

Jin-Long Pan¹, Tuan-Qing Liu, Chao Chen, Quan-Zhe Li, Wei Jiang, Tong-Mei Ding, Zhi-Qiang Yan, Guo-Dong Zhu

Affiliation

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China. dtm@sjtu.edu.cn zhuguodong1206@sjtu.edu.cn.

PMID: 31517383
DOI: 10.1039/c9ob01553a

Abstract

Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).

Publication types

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