Rhodium-Catalyzed Regioselective C–H Amidation of Benzaldehydes with Dioxazolones: Weakly Coordinating Aldehyde as a Traceless Directing Group

A rhodium-catalyzed C-H amidation of <i>ortho</i>/<i>para</i>-substituted benzaldehydes with dioxazolones has been developed to afford <i>meta</i>-substituted aromatic amides in moderate to good yields. This transformation proceeds via weakly coordinating aldehyde-directed <i>ortho</i>-C-H functionalization and concomitant decarbonylation processes. The aldehyde group notably serves as a unique traceless directing group that effectively controls the regioselectivity of the reaction. This protocol features operational simplicity and avoids the need for a transient directing group.

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Publication Details

Journal
Organic Letters
Published
2025-12-12
DOI
https://doi.org/10.1021/acs.orglett.5c04244
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.87
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article

Rhodium-Catalyzed Regioselective C–H Amidation of Benzaldehydes with Dioxazolones: Weakly Coordinating Aldehyde as a Traceless Directing Group

Zhong‐Wen Liu, Jing-Wen Jia, Xian‐Ying Shi, Juan Fan et al.
2 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.87
article

Rhodium-Catalyzed Regioselective C–H Amidation of Benzaldehydes with Dioxazolones: Weakly Coordinating Aldehyde as a Traceless Directing Group

Zhong‐Wen Liu, Jing-Wen Jia, Xian‐Ying Shi, Juan Fan, Xuanhua Chen
article en
2 citations

Abstract

A rhodium-catalyzed C-H amidation of <i>ortho</i>/<i>para</i>-substituted benzaldehydes with dioxazolones has been developed to afford <i>meta</i>-substituted aromatic amides in moderate to good yields. This transformation proceeds via weakly coordinating aldehyde-directed <i>ortho</i>-C-H functionalization and concomitant decarbonylation processes. The aldehyde group notably serves as a unique traceless directing group that effectively controls the regioselectivity of the reaction. This protocol features operational simplicity and avoids the need for a transient directing group.

Organic LettersVol. 27(51)
Key Laboratory of Guangdong Province (CN), Shaanxi Normal University (CN)
Openalex Percentile: Top 13%
Catalytic C–H Functionalization Methods
1.87
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