Electrooxidative α-hydroxymethylation of ketones with dimethylformamide as the carbon source

Zheng, Jin-Ming; Li, Yifei; Pan, Yi-Xiang; Hu, Xiaodong; Ye, Xiaoxia; Li, Renhao

doi:10.1039/d3gc00144j

Cited by 8 publications

(1 citation statement)

References 46 publications

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“…5 In recent years, electrochemical methods have attracted wide attention and have been successfully applied. 6 Among them, electrochemical oxidation and sulfonation reactions have been able to construct various sulfonated aromatic hydrocarbons well. 7 Based on our continuous interest in developing electrochemical transformations, 8 we speculated that it may be feasible to functionalize BODIPYs under mild electrochemical conditions based on radical–radical cross-coupling reactions, although such reactions have been rarely explored.…”

Section: Introductionmentioning

confidence: 99%

An electrochemical method for direct sulfonylation of BODIPYs under green conditions

Chen,

Li,

Liu

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

An electrochemical method for direct sulfonylation of BODIPYs under green conditions

Chen,

Li,

Liu

et al. 2024

Org. Chem. Front.

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Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines

La‐ongthong,

Chantarojsiri,

Soorukram

et al. 2024

Chemistry An Asian Journal

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A benign electrochemical method to access 6‐methylphenanthridines from 2‐isocyanobiaryls using N,N‐dimethylformamide (DMF) as a methyl source is reported. The protocol operates at ambient temperature without the need for harmful methylating reagents. Mechanistic studies suggested that DMF delivered a methylene synthon, followed by reduction at the cathode and tautomerization. The method offers environmental benefits by avoiding metal‐based reagents and harsh conditions.

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Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Govindan,

Jayaram,

Seenivasan

et al. 2024

ChemCatChem

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Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field of synthetic chemistry has prioritized these compounds, directing considerable research endeavour toward developing efficient and concise methodologies for their synthesis. Consequently, there is a growing interest in pioneering novel synthetic approaches to fabricate these immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, and environmental sustainability. This review sheds light on the recent advancements in the utilization of collective solvents such as methanol (alongside other alcohols), N,N‐dimethylethanolamine (DMEA), and triethylamine (TEA) (in conjunction with other amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), and dimethylformamide (DMF) as C1 synthons, serving as foundational units for the synthesis of N‐heterocycles, including quinazolinone, quinazoline, quinoxaline, pyridine, and pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, and solvents as carbon synthons or reagents, as reported in the literature, have been explored.

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Electrooxidative α-hydroxymethylation of ketones with dimethylformamide as the carbon source

Abstract: An environmentally benign electrochemical approach has been developed for the α-hydroxymethylation of ketones using N,N-dimethylformamide as the carbon source for the construction of β-hydroxy ketones. This method does not require...

Cited by 8 publications

References 46 publications

An electrochemical method for direct sulfonylation of BODIPYs under green conditions

An electrochemical method for direct sulfonylation of BODIPYs under green conditions

Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines

Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

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