Transition Metal-Controlled Divergent Annulations of Azomethine Imines with Iodonium Ylides -Centered [1,2]-Rearrangement.

Org Lett

Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450052, P. R. China.

Published: April 2023


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Article Abstract

Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides -centered [1,2]-rearrangement have been developed. The azomethine imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition and generated bicyclic diaziridine, which facilitated the -centered [1,2]-rearrangement and subsequent divergent annulations in the presence of different metal complexes as the catalysts. The benzo[]chromen-1-one and pyrano[]isochromene scaffolds could be independently constructed with Rh(III) and Ru(II), respectively. It was worth noting that the azomethine imino group was employed first as the switchable DG through rearrangement progress.

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http://dx.doi.org/10.1021/acs.orglett.3c00472DOI Listing

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