Facile access to 2,2-diaryl 2H-chromenes through a palladium-catalyzed cascade reaction of ortho-vinyl bromobenzenes with N-tosylhydrazones

Heng Zhang; Yinghua Yu; Xueliang Huang

doi:10.1039/d0ob00978d

Facile access to 2,2-diaryl 2H-chromenes through a palladium-catalyzed cascade reaction of ortho-vinyl bromobenzenes with N-tosylhydrazones

Org Biomol Chem. 2020 Jul 15;18(27):5115-5119. doi: 10.1039/d0ob00978d.

Authors

Heng Zhang¹, Yinghua Yu², Xueliang Huang¹

Affiliations

¹ Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Fujian College, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China. huangxl@fjirsm.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
² Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Fujian College, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China. huangxl@fjirsm.ac.cn.

PMID: 32596707
DOI: 10.1039/d0ob00978d

Abstract

A palladium-catalyzed cascade reaction of ortho-vinyl bromobenzenes with N-tosylhydrazones has been developed, which provides a facile approach to 2,2-disubstituted 2H-chromenes. The migration of palladium from the aryl to vinyl position is crucial, as the in situ produced vinyl palladium intermediate could further react with diazo compounds to generate the reactive species for the sequential annulation.