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...
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Published in | ACS omega Vol. 7; no. 6; pp. 5069 - 5078 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
15.02.2022
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Online Access | Get full text |
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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. |
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ISSN: | 2470-1343 2470-1343 |
DOI: | 10.1021/acsomega.1c06031 |