Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

Mai, Wenpeng; Sui, Hong‐Da; Lv, Mingxiu; Lü, Kui

doi:10.1177/17475198211028114

Journal of Chemical Research

2021

DOI: 10.1177/17475198211028114

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Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

Wenpeng Mai

Hong‐Da Sui

Mingxiu Lv

et al.

Abstract: Aryl thioesters are synthesized via nickel-catalyzed carbonylation of thioacetates with aryl iodides. Alkyl thioacetates undergo coupling with carbon monoxide and aryl iodides to produce the desired aryl thioesters in moderate yields. This catalytic carbonylative coupling process provides a cost-effective and direct approach for the preparation of useful thioesters.

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Cited by 7 publications

(1 citation statement)

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“…3 S m/z [M + H] + : 255.1049; found: 255.1049. S-Butyl 3,5-Dimethylbenzothioate (3k) 32. Eluent: V PET /V 13 C{1 H} NMR (100 MHz, CDCl 3 ) δ 192.4, 138.3, 137.4, 134.9, 124.9, 31.7, 28.7, 22.1, 21.2, 13.7.S-Butyl 3,.…”

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confidence: 99%

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Wang

Sun

et al. 2023

J. Org. Chem.

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The first example of catalytic thiocarbonylation of aryl iodides using CO2 has been achieved employing a combination of PdCl2 and carbazole-derived phosphine ligands. Under mild conditions, a broad scope of aryl iodides were converted to the desired thioester products in the presence of aryl or alkyl thiols (33 examples, up to 96% yields). The choice of metal, ligands, and reductant were crucial for high efficiency and chemoselectivity. Moreover, this strategy provided an effective method for the late-stage functionalization of biorelevant molecules.

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confidence: 99%

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Wang

Sun

et al. 2023

J. Org. Chem.

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Recent Advances in Nickel Catalyzed Carbonylative Reactionsviathe Insertion of Carbon Monoxide^†

Chen,

Lian

2023

Chin. J. Chem.

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Comprehensive SummaryCarbonyl compounds have attracted considerable attention due to their extensive applications in drug discovery. Furthermore, they are important synthetic intermediates for the construction of carbon‐carbon and carbon‐heteroatom bonds. Transition‐metal‐catalyzed carbonylation via the insertion of CO is one of the most efficient and straightforward strategies to access carbonyl compounds. However, most of the transition‐metal‐catalyzed carbonylative reactions require expensive and toxic noble‐metal catalysts. Therefore, there is a growing demand for the exploration of nickel‐catalyzed carbonylative reactions via the insertion of CO due to the earth abundance and low cost of nickel. Compared with the well‐established palladium‐catalyzed carbonylative reactions, nickel‐catalyzed analogous transformations have been relatively underdeveloped. This is primarily because CO strongly binds to nickel, often resulting in catalyst poisoning. In recent years, some research groups have focused on using CO surrogates or NN2 pincer nickel catalyst to circumvent the formation of Ni(CO)4. Nickel‐catalyzed carbonylation has been applied in the construction of carbonyl‐containing compounds, such as ketones, carboxylic acids, thioesters, acyl chloride and carboxamides.

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Nickel‐Catalyzed Synthesis of Thioesters from Amides and Disulfides

Mai,

Zhao,

et al. 2024

Eur J Org Chem

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A novel nickel‐catalyzed practical and simple synthesis of thioesters from amides and disulfides has been developed. Diverse substituted aromatic amides are capable of coupling with diaryl or dialkyl disulfides via C‐N/S‐S bonds cleavage to produce the desirable thioesters in moderate to good yields. This procedure features cheap metals, novel and easily preparative substrates, providing a simple and practical access to a variety of thioesters without toxic thiols or CO gas.

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Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

Cited by 7 publications

References 21 publications

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Recent Advances in Nickel Catalyzed Carbonylative Reactionsviathe Insertion of Carbon Monoxide^†

Nickel‐Catalyzed Synthesis of Thioesters from Amides and Disulfides

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Product

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About

Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

Cited by 7 publications

References 21 publications

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO2

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO2

Recent Advances in Nickel Catalyzed Carbonylative Reactionsviathe Insertion of Carbon Monoxide†

Nickel‐Catalyzed Synthesis of Thioesters from Amides and Disulfides

Contact Info

Product

Resources

About

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO₂

Recent Advances in Nickel Catalyzed Carbonylative Reactionsviathe Insertion of Carbon Monoxide^†