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Issue 20, 2020
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Biaryl and atropisomeric biaryl aldehyde synthesis by one-step, metal-free benzannulation of aryl enals and propiolates

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Abstract

A new method involving the benzannulation of aromatic enals and two alkyl propiolate molecules has been developed as a powerful route to biaryl aldehydes simply via the promotion of dimethyl amine. The benzannulation process in the absence of an oxidant additive tolerates successfully the formyl group in the enal component, leading to a straightforward one-step synthesis of biaryl and atropisomeric aldehydes. An enamine activation based on the aza-Michael addition of dimethyl amine to the propiolate and the amine elimination-based generation of cyclohexadiene intermediate constitute the major factors enabling the titled reactions.

Graphical abstract: Biaryl and atropisomeric biaryl aldehyde synthesis by one-step, metal-free benzannulation of aryl enals and propiolates

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Article information


Submitted
17 Aug 2020
Accepted
21 Sep 2020
First published
23 Sep 2020

Green Chem., 2020,22, 6773-6777
Article type
Communication

Biaryl and atropisomeric biaryl aldehyde synthesis by one-step, metal-free benzannulation of aryl enals and propiolates

D. Hu, L. Yang and J. Wan, Green Chem., 2020, 22, 6773
DOI: 10.1039/D0GC02806A

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