Palladium-Catalyzed Decarbonylative Michaelis–Arbuzov Reaction of Carboxylic Acids and Triaryl Phosphites

A Pd-catalyzed decarbonylative Michaelis-Arbuzov reaction of carboxylic acids and triaryl phosphites for preparing aryl phosphonates under anhydride-free conditions has been reported. In this context, triaryl phosphites serve as both reagents for activating the carboxylic acids and substrates for the reaction. There have been no reports to date of efficient and direct methods for the <i>in situ</i> activation of carboxylic acids using triaryl phosphites. In comparison to known methods, this reaction avoids the use of organohalides and has an excellent functional group tolerance for the synthesis of various aryl phosphonates from triaryl phosphites and carboxylic acids. This reaction is scalable and applicable to the synthesis of aryl phosphonates featuring bioactive fragments.

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Publication Details

Journal
Organic Letters
Published
2024-08-12
DOI
https://doi.org/10.1021/acs.orglett.4c02495
Citations
4
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
1.00

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article

Palladium-Catalyzed Decarbonylative Michaelis–Arbuzov Reaction of Carboxylic Acids and Triaryl Phosphites

Mengjie Cen, Li‐Biao Han, Zhixuan Xu, Tianzeng Huang et al.
4 citations
Organic Letters
Catalytic Cross-Coupling Reactions
1.00
article

Palladium-Catalyzed Decarbonylative Michaelis–Arbuzov Reaction of Carboxylic Acids and Triaryl Phosphites

Mengjie Cen, Li‐Biao Han, Zhixuan Xu, Tianzeng Huang, Bencan Tang, Tieqiao Chen, Linbin Yao, Zihan Chen, Long Liu, Chunya Li
article en
4 citations

Abstract

A Pd-catalyzed decarbonylative Michaelis-Arbuzov reaction of carboxylic acids and triaryl phosphites for preparing aryl phosphonates under anhydride-free conditions has been reported. In this context, triaryl phosphites serve as both reagents for activating the carboxylic acids and substrates for the reaction. There have been no reports to date of efficient and direct methods for the <i>in situ</i> activation of carboxylic acids using triaryl phosphites. In comparison to known methods, this reaction avoids the use of organohalides and has an excellent functional group tolerance for the synthesis of various aryl phosphonates from triaryl phosphites and carboxylic acids. This reaction is scalable and applicable to the synthesis of aryl phosphonates featuring bioactive fragments.

Organic LettersVol. 26(33)
University of Nottingham Ningbo China (CN), Shaoxing University (CN), Hainan University (CN), Institute of New Materials (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hainan Province
Openalex Percentile: Top 27%
Catalytic Cross-Coupling Reactions
1.00
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Palladium-Catalyzed Decarbonylative Michaelis–Arbuzov Reaction of Carboxylic Acids and Triaryl Phosphites — Mengjie Cen, Li‐Biao Han, et al. · Organic Letters (2024) | TGRS Research Map | TGRS