Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system

Beesu, Mallesh; Periasamy, Muthu

doi:10.1016/j.jorganchem.2012.01.005

Cited by 8 publications

(2 citation statements)

References 40 publications

(15 reference statements)

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“…Good catalytic conversion of acetylene (85%) and selectivity of acrylic acid (99%) under mild conditions (T = 40-50 °C) is achieved with a catalyst system consisting of a homogeneous catalyst Pd(OAc)2, with diphenyl-2-pyridylphospine as the phosphine ligands and trifluoromethane sulfonic acid as the acidic promoter [239]. Hydrocarboxylation of other alkynes is an important reaction for production of α,β-unsaturated carboxylic acids [240,241]. The most widely used catalyst in hydrocarboxylation of alkynes are based on Ni, Co, and Pd [242].…”

Section: Potential Existing Technologies and New Considerations For Vmentioning

confidence: 99%

Utilization of Volatile Organic Compounds as an Alternative for Destructive Abatement

et al. 2015

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Abstract:The treatment of volatile organic compounds (VOC) emissions is a necessity of today. The catalytic treatment has already proven to be environmentally and economically sound technology for the total oxidation of the VOCs. However, in certain cases, it may also become economical to utilize these emissions in some profitable way. Currently, the most common way to utilize the VOC emissions is their use in energy production. However, interesting possibilities are arising from the usage of VOCs in hydrogen and syngas production. Production of chemicals from VOC emissions is still mainly at the research stage. However, few commercial examples exist. This review will summarize the commercially existing VOC utilization possibilities, present the utilization applications that are in the research stage and introduce some novel ideas related to the catalytic utilization possibilities of the VOC emissions. In general, there exist a vast number of possibilities for VOC OPEN ACCESSCatalysts 2015, 5 1093 utilization via different catalytic processes, which creates also a good research potential for the future.

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Section: Potential Existing Technologies and New Considerations For Vmentioning

confidence: 99%

Utilization of Volatile Organic Compounds as an Alternative for Destructive Abatement

et al. 2015

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“…The alkyne bond has been realised as an intrinsic functional group due to its propensity for conversion through transformations such as carboxylation, hydro‐amination and addition to electrophiles . Electron‐rich alkyne substrates enable the construction of drug scaffolds, normally unavailable from conventional synthetic approaches and a number of catalytic systems have been developed to synthesise polycyclic heterocycles from alkynes as enhanced fluorescence probes .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of Fused Heterocyclic Molecular Rods: A Combined Experimental and Theoretical Study on Diethynyl Dithienothiophenyl Derivatives

et al. 2017

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A structural and electronic diversity of symmetric diethynyl dithienothiophenyl (DTT) molecular rods were synthesised and their properties fully characterised using optical and thermal analysis and complemented with density functional theory (DFT) calculations. It was found that some structures are stable up to 381 °C. Due to the nature of both the derivative and the substituent, physical properties such as electron donating ability and thermal stability can be fine‐tuned to generate rationally designed materials, all of which have excellent solubility in common organic solvents. The single‐crystal x‐ray structures revealed that both bulky silyl and linear alkyl derivatives generate regular lateral close packing between the adjacent molecules, suitable for charge‐transfer in organic thin‐film transistors (OTFTs), whereas the same ethynyl derivative without an alkyl chain gives a non‐planar interlinking structure and thus unsuitable for OTFTs. These air‐stable electron rich DTT‐based molecular rods have strong potential as organic semiconductors for organic electronic applications.

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Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel‐Catalyzed Cascade Reactions: Facile Synthesis of Profens

et al. 2021

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We report a stereoselective conversion of terminal alkynes to a-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (> 90 % ees) and the chiral fragment of AZD2716.

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Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system

Cited by 8 publications

References 40 publications

Utilization of Volatile Organic Compounds as an Alternative for Destructive Abatement

Utilization of Volatile Organic Compounds as an Alternative for Destructive Abatement

Synthesis and Characterisation of Fused Heterocyclic Molecular Rods: A Combined Experimental and Theoretical Study on Diethynyl Dithienothiophenyl Derivatives

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel‐Catalyzed Cascade Reactions: Facile Synthesis of Profens

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