Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions

Lin, Feng; Feng, Qiang; Cui, Xiuling; Song, Qiuling

doi:10.1039/c3ra43615b

Cited by 12 publications

(9 citation statements)

References 18 publications

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“…Similar types of reactions were reported with pyridine, pyrrole, carboxylic acids or aldehydes using DCM as methylene source for the construction of bis‐type molecules. Recently, Liu et al .…”

Section: Reaction Solvents As Precursors For the Installation Of Key supporting

confidence: 56%

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

2019

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The solvent is an important entity in a chemical reaction, generally, required for the effective collision of the reactant molecules. By looking at the chemical nature, physic-chemical properties, and more importantly, smart selection, reaction solvents attract synthetic chemists for their effective use as reagents in a chemical reaction. For the installation of small key functionalities in the molecules, reaction solvents provide attractive, atom-economical, greener, and also less costly alternatives to other reagent-based strategies. For instance, particular reaction solvents can serve as a multipurpose building block for various units, such as O,

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Section: Reaction Solvents As Precursors For the Installation Of Key supporting

confidence: 56%

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

2019

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“…Remarkably, when dichloroethane (DCE) was introduced as a congener of bifunctional alkyl halide under the standard reaction conditions, the monoester product 4 s was obtained exclusively in 50% yield. Previously efforts have been given to synthesize such monoesters in the mixed solvent system starting from aldehyde and di‐chloroalkane (mainly DCM, DCE, DCP) at elevated temperature (120 °C for 5 hr after that 90 °C for 2.5 hr) using TBHP as an oxidant [17] . However, our methodology offers an atom and step‐economic route for the selective conversion of aldehyde into monoester 4 s within a short time span of 3 hr at 80 °C.…”

Section: Resultsmentioning

confidence: 99%

“…Previously efforts have been given to synthesize such monoesters in the mixed solvent system starting from aldehyde and di-chloroalkane (mainly DCM, DCE, DCP) at elevated temperature (120 °C for 5 hr after that 90 °C for 2.5 hr) using TBHP as an oxidant. [17] However, our methodology offers an atom and step-economic route for the selective conversion of aldehyde into monoester 4 s within a short time span of 3 hr at 80 °C.…”

Section: Resultsmentioning

confidence: 99%

Copper Catalyzed‐TBHP/DTBP Promoted C(sp²)−H Bond Scission of Aldehydes: An Approach to Transform Aldehyde to Esters

2021

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The direct oxidative C(sp2)−H functionalization represents a step and atom economical approach for the utilization of aldehyde as promising acyl surrogates. A mild and practical copper catalyzed‐TBHP/DTBP promoted esterification of aldehydes in the presence of alkyl halides and alcohols has been developed. This strategy relies on naturally abundant aldehydes as acyl precursors, which can further couple with readily available alkyl halides/alcohols to transform into esters. Preliminary mechanistic investigations reveal that aldehyde in the presence of tert‐butoxy radical transforms into acyl radical. This protocol exhibits a broad substrate scope along with wide functional group compatibility and is applicable to a wide range of aldehydes, including challenging aliphatic aldehydes to undergo the C(sp2)−H bond scission to furnish the desired esters in good to excellent yields.

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“…Currently, the reaction of CH 2 I 2 , CH 2 Br 2 , or CH 2 Cl 2 with a carboxylic acid constitutes the prominent approach in the synthesis of methylene‐bridged bis‐carboxylates (Scheme A). The major restriction of such direct double nucleophilic substitution reaction lies in the product diversity associated with the only possible variation in carboxylic acid substrate.…”

Section: Methodsmentioning

confidence: 99%

Direct Synthesis of Methylene‐Bridged Bis‐biaryl Carboxylates via Cascade Suzuki Coupling and CH₂Cl₂‐Based Bis‐esterification

et al. 2018

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The multicomponent reactions of iodobenzoic acids, aryl boronic acids, and dichloromethane (DCM) have been designed for the synthesis of various methylene‐bridged bis‐biaryl functionalized carboxylates. Under the catalysis of Pd(OAc)2, the formation of the products involves the cascade Suzuki coupling and CH2Cl2‐base bis‐esterification. The present work offers a direct and practical route to the synthesis of novel carboxylate scaffolds with extended diversity.

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Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions

Cited by 12 publications

References 18 publications

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Copper Catalyzed‐TBHP/DTBP Promoted C(sp²)−H Bond Scission of Aldehydes: An Approach to Transform Aldehyde to Esters

Direct Synthesis of Methylene‐Bridged Bis‐biaryl Carboxylates via Cascade Suzuki Coupling and CH₂Cl₂‐Based Bis‐esterification

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Synthesis of esters from aldehydes or carboxylic acids with dichloromethane, dichloroethane or dichloropropane under mild conditions

Cited by 12 publications

References 18 publications

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Copper Catalyzed‐TBHP/DTBP Promoted C(sp2)−H Bond Scission of Aldehydes: An Approach to Transform Aldehyde to Esters

Direct Synthesis of Methylene‐Bridged Bis‐biaryl Carboxylates via Cascade Suzuki Coupling and CH2Cl2‐Based Bis‐esterification

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Resources

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Copper Catalyzed‐TBHP/DTBP Promoted C(sp²)−H Bond Scission of Aldehydes: An Approach to Transform Aldehyde to Esters

Direct Synthesis of Methylene‐Bridged Bis‐biaryl Carboxylates via Cascade Suzuki Coupling and CH₂Cl₂‐Based Bis‐esterification