Syngas-Mediated C-C Bond Formation in Flow: Selective Rhodium-Catalysed Hydroformylation of Styrenes

Kasinathan, Sivarajan; Bourne, Samuel L.; Tolstoy, Päivi; Koóš, Peter; O’Brien, Matthew; Bates, Roderick W.; Baxendale, Ian R.; Ley, Steven V.

doi:10.1055/s-0031-1289292

Cited by 21 publications

(3 citation statements)

References 9 publications

(11 reference statements)

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“…Decreasing pressure of the hydroformylation reactions catalyzed by Rh I complexes of L1 or L3 , from 20 atm to 5 atm, at 80 °C increased the n ‐selectivity from 24.8 % to 51.3 % and from 20.55 % to 47.9 %, respectively. Increased n ‐selectivity with reduced pressure in hydroformylation reactions has previously been reported in the literature,, , , , , , and has been attributed to different rate laws at different pressures. As Landis has demonstrated, decreasing pressures to very low values can increase the amount of n ‐aldehyde produced .…”

Section: Resultsmentioning

confidence: 62%

Comparative Study of Novel Phosphordiamidite and Phosphite Ligands Used in Alkene Hydroformylation; Synthesis, Characterization, Metalation, and Catalytic Evaluation

et al. 2018

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Three novel ligands have been prepared by the reactions of 1,1′-(chlorophosphinediyl)bis(1H-pyrrole) with either 2pyridinemethanol or 2,6-pyridinedimethanol or the reaction of 1,1′-biphenyl-2,2′-diyl phosphorochloridite with 2-pyridinemethanol. Measurement of | 1 J P-Se | values demonstrate that the phosphite donor is less basic than the phosphoramidite donors. Coordination preferences of the ligands in octahedral cis-tetracarbonylmolybdenum(0) and square planar cis-dichloropalladium(II) complexes have been evaluated using multinuclear NMR and X-ray crystallography. Rhodium(I) complexes of the Scheme 2. Synthesis of chelating molybdenum complexes 1-3.Scheme 3. Synthesis of palladium chelating complexes 4, 5 and 6.

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Section: Resultsmentioning

confidence: 62%

Comparative Study of Novel Phosphordiamidite and Phosphite Ligands Used in Alkene Hydroformylation; Synthesis, Characterization, Metalation, and Catalytic Evaluation

et al. 2018

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“…In 2011, Ley and co-workers developed a flow reactor for the hydroformylation of styrenes based upon gas addition using a tube-in-tube reactor system [556]. The reactor was highly efficient (81-97% conversion) and flexible (12 examples).…”

Section: Hydroformylationmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…Microfluidic strategies, including both continuous − and single-droplet flow reactors, ,− with enhanced heat and mass transfer rates, enhanced safety, precise process control, well-defined interfacial areas, and highly efficient chemical consumption rates have recently been promoted as an effective approach for fundamental and applied studies of gas–liquid processes including hydrogenation, − glycosylation, , carbonylation, − diazomethanation, difluoromethylation, oxygenation, − carboxylation, , photoredox catalysis, − borylation, , and hydroformylation. ,, Specifically, microfluidic platforms have been utilized for fundamental investigations of physical/chemical processes involving CO 2 for applications such as CO 2 capture and storage and material synthesis . When dealing with relatively long processing times (>1 min), the unique benefits of microscale fluidic processing allow accurate in situ studies of chemical reactions by simply using a single microliter droplet oscillating within a microchannel .…”

Section: Introductionmentioning

confidence: 99%

Accelerated Material-Efficient Investigation of Switchable Hydrophilicity Solvents for Energy-Efficient Solvent Recovery

Han

Raghuvanshi

Abolhasani

2020

ACS Sustainable Chem. Eng.

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In most chemical industries, solvent removal and recovery processes are heavily dependent on hazardous volatile solvents with energy-intensive distillation processes because of their ease of separation. An emerging promising alternative is implementing switchable solvents with on-demand and reversible switching of their physiochemical properties triggered by carbon dioxide (CO 2 ). Utilization and widespread implementation of switchable solvents can dramatically reduce environmental risks and energy requirements for solvent removal and recovery processes. Despite intriguing characteristics of switchable solvents, the time-and material-intensive nature of conventional batch strategies has hindered a comprehensive understanding of this exciting class of green solvents. Herein, we report an accelerated time-and material-efficient (green) flow chemistry strategy for in situ fundamental and applied studies of CO 2 -mediated switchable solvents. Utilizing a highly gas-permeable membrane microreactor increases the gas−liquid interfacial area for CO 2 injection, thereby enhancing the gas−liquid mass transfer (∼60 times faster equilibrium time than a batch reactor), while minimizing the chemical consumption (∼1000 times less than a batch reactor) and waste generation (∼1500 times less than a batch reactor) for each solventswitching experiment. Utilizing the developed green flow chemistry strategy, we comprehensively study the effects of continuous and discrete process parameters on the efficiency and kinetics of hydrophilicity switching of switchable solvents. The intensified CO 2triggered switchable hydrophilicity solvent extraction process allows accurate material-efficient studies of switchable solvents and therefore will accelerate the development and adoption of distillation-free, green, and sustainable solvent recovery strategies in chemical industries.

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Syngas-Mediated C-C Bond Formation in Flow: Selective Rhodium-Catalysed Hydroformylation of Styrenes

Abstract: We report a continuous flow, rhodium-catalysed hydroformylation of various styrenes using a tube-in-tube gas-liquid reactor. The flow process afforded selectively branched aryl aldehydes in good yields.

Cited by 21 publications

References 9 publications

Comparative Study of Novel Phosphordiamidite and Phosphite Ligands Used in Alkene Hydroformylation; Synthesis, Characterization, Metalation, and Catalytic Evaluation

Comparative Study of Novel Phosphordiamidite and Phosphite Ligands Used in Alkene Hydroformylation; Synthesis, Characterization, Metalation, and Catalytic Evaluation

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Accelerated Material-Efficient Investigation of Switchable Hydrophilicity Solvents for Energy-Efficient Solvent Recovery

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