Development of non-gaseous palladium-catalyzed carbonylative cross-coupling reaction

<p indent="0mm">Palladium-catalyzed carbonylation coupling reaction has become an important method for the synthesis of carbonyl compounds in modern organic synthesis. However, due to the high toxicity of carbon monoxide gas and the difficulty in manipulating it, the use of non-gas carbonyl source surrogates to construct green, safe and controllable carbonylation reaction systems has become a hot direction in the field of carbonylation coupling reaction research. In this paper, three main types of non-gas carbonyl sources, organic small molecules, carboxylic acid derivatives and transition metal carbonyl compounds, are reviewed in terms of release conditions, release modes, carbonyl utilization efficiency and applicable reaction types, as well as their respective advantages and disadvantages in palladium-catalyzed carbonylation coupling reaction. A summary of the literatures suggest that transition metal carbonyl compounds, with the advantages of high carbonyl loading, the ability to achieve <italic>in situ</italic> CO release and the applicability to different types of carbonylation reactions, have a wider research potential in the field of organic synthesis, while further studies should focus on the search for new decarbonylation and the release mechanisms, the modulation of non-carbonyl by-product compositions and the influence of low-valent metal species on the palladium-catalyzed reactions.

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Publication Details

Journal
Scientia Sinica Chimica
Published
2024-09-27
DOI
https://doi.org/10.1360/ssc-2024-0125
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Development of non-gaseous palladium-catalyzed carbonylative cross-coupling reaction

Ziwei Gao, Lei Fan, Yajun Jian, Quan Gu et al.
Scientia Sinica Chimica
Catalytic C–H Functionalization Methods
article

Development of non-gaseous palladium-catalyzed carbonylative cross-coupling reaction

Ziwei Gao, Lei Fan, Yajun Jian, Quan Gu, Yanyan Wang, Weiqiang Zhang, Hongyu Yang, Meng Guo, Huangming Sun
article en

Abstract

<p indent="0mm">Palladium-catalyzed carbonylation coupling reaction has become an important method for the synthesis of carbonyl compounds in modern organic synthesis. However, due to the high toxicity of carbon monoxide gas and the difficulty in manipulating it, the use of non-gas carbonyl source surrogates to construct green, safe and controllable carbonylation reaction systems has become a hot direction in the field of carbonylation coupling reaction research. In this paper, three main types of non-gas carbonyl sources, organic small molecules, carboxylic acid derivatives and transition metal carbonyl compounds, are reviewed in terms of release conditions, release modes, carbonyl utilization efficiency and applicable reaction types, as well as their respective advantages and disadvantages in palladium-catalyzed carbonylation coupling reaction. A summary of the literatures suggest that transition metal carbonyl compounds, with the advantages of high carbonyl loading, the ability to achieve <italic>in situ</italic> CO release and the applicability to different types of carbonylation reactions, have a wider research potential in the field of organic synthesis, while further studies should focus on the search for new decarbonylation and the release mechanisms, the modulation of non-carbonyl by-product compositions and the influence of low-valent metal species on the palladium-catalyzed reactions.

Scientia Sinica ChimicaVol. 54(10)
Openalex Percentile: Top 88%
Catalytic C–H Functionalization Methods
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Development of non-gaseous palladium-catalyzed carbonylative cross-coupling reaction — Ziwei Gao, Lei Fan, et al. · Scientia Sinica Chimica (2024) | TGRS Research Map | TGRS