Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy

Herein, we describe a dual catalytic strategy that employs dihydroquinazolinones, derived from ketone analogs, as versatile intermediates for acylation via α C-C cleavage with 2-pyridyl esters, facilitating the efficient synthesis of a variety of ketones. The reaction accommodates a wide range of ketones and carboxylic acids, showing tolerance to various functional groups. The versatility of this synthetic technique is further highlighted through its application in the late-stage modification of pharmaceuticals and biologically active natural products.

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Publication Details

Journal
Organic Letters
Published
2024-10-28
DOI
https://doi.org/10.1021/acs.orglett.4c03456
Citations
10
Primary Topic
Click Chemistry and Applications
Type
article
Field-Weighted Citation Impact
2.50

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article

Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy

Y. George Zheng, Fei Pan, J. Paul Chen, Ke‐Han He et al.
10 citations
Organic Letters
Click Chemistry and Applications
2.50
article

Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy

Y. George Zheng, Fei Pan, J. Paul Chen, Ke‐Han He, Na Jin
article en
10 citations

Abstract

Herein, we describe a dual catalytic strategy that employs dihydroquinazolinones, derived from ketone analogs, as versatile intermediates for acylation via α C-C cleavage with 2-pyridyl esters, facilitating the efficient synthesis of a variety of ketones. The reaction accommodates a wide range of ketones and carboxylic acids, showing tolerance to various functional groups. The versatility of this synthetic technique is further highlighted through its application in the late-stage modification of pharmaceuticals and biologically active natural products.

Organic LettersVol. 26(44)
Xichang University (CN), Sichuan Normal University (CN)
National Natural Science Foundation of China, Sichuan Province Science and Technology Support Program
Openalex Percentile: Top 11%
Click Chemistry and Applications
2.50
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Ketone Skeletal Modification via a Metallaphotoredox-Catalyzed Deacylation and Acylation Strategy — Y. George Zheng, Fei Pan, et al. · Organic Letters (2024) | TGRS Research Map | TGRS