Acetic anhydride as a versatile carbon source in carbonylation reactions

Acetic anhydride (Ac<sub>2</sub>O) is a cheap and easily available chemical feedstock that is widely used as an acetylating or dehydrating agent in organic synthesis. Here, we report Ac<sub>2</sub>O as a novel and versatile carbon source in carbonylation reactions. Notably, besides CO, the acetic acid (AcOH), decomposed from the Ac<sub>2</sub>O molecule, could participate in the reaction and simultaneously act as a necessary cosolvent. Acetate esters, aldehydes, and carboxylic acids could be produced separately by simply regulating the Pd-catalyzed reaction of olefins, Ac<sub>2</sub>O and H<sub>2</sub>. Remarkably, the reaction is applicable to various olefins, and high yields (up to 95%) as well as good regioselectivities of the acetate esters and aldehydes could be achieved. The outstanding results of acetate ester synthesis represent a successful and innovative cascade reaction, which demonstrates good atom economy. The mechanism of the reactions, especially the Ac<sub>2</sub>O decomposition, has been studied by control experiments and DFT calculations. This work opens a new avenue for carbonylation reactions.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc06323j
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Acetic anhydride as a versatile carbon source in carbonylation reactions

Jia Guo, Tianbin Wu, Tong Xing, Chenglong Yu et al.
Chemical Science
Catalytic Cross-Coupling Reactions
article

Acetic anhydride as a versatile carbon source in carbonylation reactions

Jia Guo, Tianbin Wu, Tong Xing, Chenglong Yu, Ying Wang, Yanru Zhang, Junfeng Xiang, Jun He, Jie Cui, Ziwei Zhao, Longbo Zhang, Qingli Qian, Buxing Han, Yanyan Wang
article en

Abstract

Acetic anhydride (Ac<sub>2</sub>O) is a cheap and easily available chemical feedstock that is widely used as an acetylating or dehydrating agent in organic synthesis. Here, we report Ac<sub>2</sub>O as a novel and versatile carbon source in carbonylation reactions. Notably, besides CO, the acetic acid (AcOH), decomposed from the Ac<sub>2</sub>O molecule, could participate in the reaction and simultaneously act as a necessary cosolvent. Acetate esters, aldehydes, and carboxylic acids could be produced separately by simply regulating the Pd-catalyzed reaction of olefins, Ac<sub>2</sub>O and H<sub>2</sub>. Remarkably, the reaction is applicable to various olefins, and high yields (up to 95%) as well as good regioselectivities of the acetate esters and aldehydes could be achieved. The outstanding results of acetate ester synthesis represent a successful and innovative cascade reaction, which demonstrates good atom economy. The mechanism of the reactions, especially the Ac<sub>2</sub>O decomposition, has been studied by control experiments and DFT calculations. This work opens a new avenue for carbonylation reactions.

Chemical ScienceVol. 16(48)
Sinopec (China) (CN), Chinese Academy of Sciences (CN), Beijing National Laboratory for Molecular Sciences (CN), Institute of Chemistry (CN), University of Chinese Academy of Sciences (CN), East China Normal University (CN)
National Science Foundation, National Natural Science Foundation of China, National Key Research and Development Program of China
Openalex Percentile: Top 76%
Catalytic Cross-Coupling Reactions
DOIOpen Access PDFOpenAlex
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