Sequential catalytic functionalization of aryltriazenyl aldehydes for the synthesis of complex benzenes

We demonstrate that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed...

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Bibliographic Details
Main Authors: Seo, S, Gao, M, Paffenholz, E, Willis, M
Format: Journal article
Language:English
Published: American Chemical Society 2021
Description
Summary:We demonstrate that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions. The resulting triazene-substituted ketone products can then undergo either a Rh(III)-catalyzed C-H activation, or an electrophilic aromatic substitution reaction, achieving multi-functionalization of the benzene core. Subsequent triazene derivatization provides traceless products