Carbonylation in microflow: close encounters of CO and reactive species

Fukuyama, Takahide; Totoki, Takenori; Ryu, Ilhyong

doi:10.1039/c3gc41789a

Cited by 124 publications

(47 citation statements)

References 64 publications

(21 reference statements)

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“…By comparison with butyric acid, β‐hydroxybutyric acid is a stronger acid in terms of the p K a values, and we speculated that a flow system using sulfonic acid functionalized silica with a β‐hydroxy function (HO‐SAS), would serve as a far better Brønsted acid catalyst for the dehydration of alcohols (Scheme ). Herein, we report the clean and fast‐flow dehydration of allylic alcohols by using a column reactor charged with an HO‐SAS catalyst with THF as the solvent. In an important development, the protocol was successfully applied to the consecutive flow synthesis of pristane by sequential dehydration and hydrogenation …”

Section: Introductionmentioning

confidence: 99%

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

et al. 2017

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Hydroxy‐substituted sulfonic acid functionalized silica (HO‐SAS) in combination with THF containing a small amount of water as a solvent proved to be a reliable system for the dehydration of allylic alcohols. This process generally caused dehydration within 1 min through a column reactor charged with HO‐SAS. The flow dehydration was sequenced by flow hydrogenation, which resulted in the synthesis of pristane. A scalable flow synthesis of pristane was successfully performed and afforded 10 g of pristane after an operation of 2 h. We also performed dehydration and hydrogenation by using a mixed column of HO‐SAS and 10 % Pd/C.

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Section: Introductionmentioning

confidence: 99%

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

et al. 2017

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“…Initially, a fixed 5 mol % of Pd(OAc) 2 and 10 mol % of the phosphine ligand was investigated. It was noted that the catalyst level could be reduced [ 34 ], but this amount allowed for an efficient catalytic process with short reaction times in the region of two hours, a good match for the flow system assembly [ 8 ]. Five different phosphine ligands were subsequently tested, three of which were monodentate with a variable cone angle ( 6 – 8 ; 145–256°) [ 35 – 36 ] and the other two bidendate phosphine ligands namely 1,4-bis(diphenylphosphino)butane (DPPB, 9 ; βn = 98°) and Xantphos ( 10 ; 104 and 133°) with differing bite angles ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

Mallia

Walter

Baxendale

2016

Beilstein J. Org. Chem.

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SummaryThe flow synthesis of ortho-substituted carboxylic acids, using carbon monoxide gas, has been studied for a number of substrates. The optimised conditions make use of a simple catalyst system compromising of triphenylphosphine as the ligand and palladium acetate as the pre-catalyst. Carbon monoxide was introduced via a reverse “tube-in-tube” flow reactor at elevated pressures to give yields of carboxylated products that are much higher than those obtained under normal batch conditions.

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“…Carbon monoxide (CO) is ah ighly valuableC 1b uilding block due to the number of carbonylation reactions available to the synthetic chemist. [23] CO is ac olorless, odorless andt asteless gas. It is highly poisonous and flammable, thusi ti su nderused for organic synthesis.…”

Section: Carbonmonoxide (Co)mentioning

confidence: 99%

Membrane Microreactors for the On‐Demand Generation, Separation, and Reaction of Gases

Hone

Kappe

2020

Chemistry A European J

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The use of gases as reagents in organic synthesis can be very challenging, particularly at al aboratory scale. This Concept takes into account recent studies to make the case that gases can indeed be efficiently and safely formed from relativelyi nexpensive commercially available reagents for use in aw ide range of organic transformations. In particular,w ea rgue that the exploitation of continuous flow membrane reactorse nables the effective separation of the chemistry necessary for gas formation from the chemistry for gas consumption, with these two stages often containing incompatible chemistry. The approach outlined eliminates the need to store and transport excessive amountso fp otentially toxic, reactive or explosive gases.T he on-demand generation, separation and reaction of an umber of gases, including carbon monoxide, diazomethane, trifluoromethyl diazomethane, hydrogen cyanide, ammonia and formaldehyde, is discussed. Gas-Liquid Membrane Microreactors Over recent years, microreactors and continuous flow technologies have emergeda sa ne nabling tool for the safe handling of hazardousc hemistry. [8, 9] In particular, for accessing "forgotten" and "forbidden" chemistry which cannotb ea ccessed under conventional batch conditions.

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Carbonylation in microflow: close encounters of CO and reactive species

Cited by 124 publications

References 64 publications

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste‐Free Synthesis of Pristane

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

Membrane Microreactors for the On‐Demand Generation, Separation, and Reaction of Gases

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