Accessing Grignard Reluctant Aldehyde in 2‑Oxoaldehyde by Organocuprates to Give [1,2] Addition and Oxidative Coupling Reactions

Novel finding of aldehyde in 2-oxoaldehyde (2OA) is presented as it unprecedentedly disinclines to react with Grignard reagents but reacts with moderate organocuprate reagents in anaerobic condition to give [1,2] addition (α-hydroxyketones) reaction. In the presence of air, the reaction produces an...

Full description

Saved in:
Bibliographic Details
Published in:ACS omega 2022-02, Vol.7 (6), p.5069-5078
Main Authors: Battula, Satyanarayana, Desai, Aman A, Soni, Jigar Y, Mehta, Dhruv P
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Novel finding of aldehyde in 2-oxoaldehyde (2OA) is presented as it unprecedentedly disinclines to react with Grignard reagents but reacts with moderate organocuprate reagents in anaerobic condition to give [1,2] addition (α-hydroxyketones) reaction. In the presence of air, the reaction produces an efficient protocol for the synthesis of 1,2-diones through a copper-catalyzed oxidative cross-coupling reaction at room temperature. Mechanistic studies indicate that α-hydroxy ketone perhaps is generated before the hydrolysis step/acid work-up process. The α-keto group of 2OA causes to exhibit this peculiar aldehyde behavior toward these organometallic reagents.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c06031