Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides

Yi Shi; Siqi Li; Yang Lu; Zizhen Zhao; Pingfan Li; Jiaxi Xu

doi:10.1039/c9cc09262e

Microwave-assisted organic acid-base-co-catalyzed tandem Meinwald rearrangement and annulation of styrylepoxides

Chem Commun (Camb). 2020 Feb 18;56(14):2131-2134. doi: 10.1039/c9cc09262e. Epub 2020 Jan 23.

Authors

Yi Shi¹, Siqi Li¹, Yang Lu¹, Zizhen Zhao¹, Pingfan Li¹, Jiaxi Xu¹

Affiliation

¹ State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China. lipf@mail.buct.edu.cn jxxu@mail.buct.edu.cn.

PMID: 31970365
DOI: 10.1039/c9cc09262e

Abstract

A novel organic acid-base-co-catalyzed conversion of styrylepoxides into [1,1'-biaryl]-3-carbaldehydes was realized under microwave irradiation. Styrylepoxides first underwent an acid-catalyzed Meinwald rearrangement followed by a tandem base-catalyzed Michael addition, aldol addition, and aromatization sequence to generate [1,1'-biaryl]-3-carbaldehydes.