Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C-H/C-C Activations

Jin-Long Pan; Chang Liu; Chao Chen; Tuan-Qing Liu; Man Wang; Zhenliang Sun; Shu-Yu Zhang

doi:10.1021/acs.orglett.9b00812

Dual Directing-Groups-Assisted Redox-Neutral Annulation and Ring Opening of N-Aryloxyacetamides with 1-Alkynylcyclobutanols via Rhodium(III)-Catalyzed C-H/C-C Activations

Org Lett. 2019 Apr 19;21(8):2823-2827. doi: 10.1021/acs.orglett.9b00812. Epub 2019 Mar 27.

Authors

Jin-Long Pan¹, Chang Liu¹, Chao Chen¹, Tuan-Qing Liu¹, Man Wang¹, Zhenliang Sun^{1

2}, Shu-Yu Zhang¹

Affiliations

¹ Shanghai Jiao Tong University Affiliated Sixth People's Hospital South Campus & Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , Shanghai 200240 , P. R. China.
² Shanghai University of Medicine & Health Sciences Affiliated Sixth People's Hospital South Campus , Shanghai 201499 , China.

PMID: 30916570
DOI: 10.1021/acs.orglett.9b00812

Abstract

A cascade [3 + 2] annulation and ring opening of N-aryloxyacetamides with 1-alkynylcyclobutanols via Rh(III)-catalyzed redox-neutral C-H/C-C activations using internal oxidative O-NHAc and -OH as the dual directing groups has been achieved. This reaction provided an efficient and regioselective approach to benzofuran derivatives with good functional group compatibility and high yields.

Publication types

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