Continuous amination of aryl/heteroaryl halides using aqueous ammonia in a Teflon AF-2400 tube-in-tube micro-flow reactor

Xue, Chengwen; Li, Jiesheng; Lee, Jin Ping; Zhang, Ping; Wu, Jie

doi:10.1039/c8re00216a

Cited by 17 publications

(8 citation statements)

References 19 publications

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“…A second work that made use of the highly controlled stoichiometry of hazardous gases in tube‐in‐tube reactions was performed by Wu, Zhang, and co‐workers [78] . They demonstrated the use of aqueous ammonia for the continuous amination of aryl and heteroaryl halides from the hypothesis that NH 3 can diffuse through the AF‐2400 tubing at elevated temperatures from readily available and safe aqueous ammonia (Scheme 9A).…”

Section: Continuous‐flow Setups For Handling Gas–liquid Reactionsmentioning

confidence: 99%

Multiphasic Continuous‐Flow Reactors for Handling Gaseous Reagents in Organic Synthesis: Enhancing Efficiency and Safety in Chemical Processes

Laporte,

Masson,

Zondag

et al. 2023

Angewandte Chemie

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The use of reactive gaseous reagents for the production of active pharmaceutical ingredients (APIs) remains a scientific challenge due to safety and efficiency limitations. The implementation of continuous‐flow reactors has resulted in rapid development of gas‐handling technology because of several advantages such as increased interfacial area, improved mass‐ and heat transfer, and seamless scale‐up. This technology enables shorter and more atom‐economic synthesis routes for the production of pharmaceutical compounds. Herein, we provide an overview of literature from 2016 onwards in the development of gas‐handling continuous‐flow technology as well as the use of gases in functionalization of APIs.

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Section: Continuous‐flow Setups For Handling Gas–liquid Reactionsmentioning

confidence: 99%

Multiphasic Continuous‐Flow Reactors for Handling Gaseous Reagents in Organic Synthesis: Enhancing Efficiency and Safety in Chemical Processes

Laporte,

Masson,

Zondag

et al. 2023

Angewandte Chemie

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“…Several more papers have since been published demonstrating this technology. 12,126,[128][129][130][131][132] Uniqsis Ltd. and Vapourtec Ltd. have also adapted this technology for commercial tube-in-tube reactors.…”

Section: Reaction Chemistry and Engineering Reviewmentioning

confidence: 99%

Application of reactor engineering concepts in continuous flow chemistry: a review

Neyt

Riley

2021

React. Chem. Eng.

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“…Zhang, Wu and co-workers recently reportedt he use of at ube-in-tube reactor for the generationo f anhydrous NH 3 from an aqueous stream of NH 3 (25 %). [37] The inner tube containeda queous NH 3 , whereas the outer tube was the locationo ft he organic reaction. Karl-Fischer titration analysisd etermined that the permeation by water was negligible when operating the tube-in-tube system at temperatures below 50 8Ca nd shorter residence times.H owever,i ts hould be noted that at highero perating temperatures the permeation of water was observed.…”

Section: Ammonia (Nh 3 )mentioning

confidence: 99%

“…Zhang, Wu and co‐workers recently reported the use of a tube‐in‐tube reactor for the generation of anhydrous NH 3 from an aqueous stream of NH 3 (25 %) . The inner tube contained aqueous NH 3 , whereas the outer tube was the location of the organic reaction.…”

Section: On‐demand Generation Separation and Reaction Of Gasesmentioning

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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Continuous amination of aryl/heteroaryl halides using aqueous ammonia in a Teflon AF-2400 tube-in-tube micro-flow reactor

Abstract: Aqueous ammonia was applied as the ammonia source in the continuous amination of aromatic and heteroaromatic halides assisted by a Teflon AF-2400 tube-in-tube reactor to generate densely substituted aryl/heteroaryl amines in high yields.

Cited by 17 publications

References 19 publications

Multiphasic Continuous‐Flow Reactors for Handling Gaseous Reagents in Organic Synthesis: Enhancing Efficiency and Safety in Chemical Processes

Multiphasic Continuous‐Flow Reactors for Handling Gaseous Reagents in Organic Synthesis: Enhancing Efficiency and Safety in Chemical Processes

Application of reactor engineering concepts in continuous flow chemistry: a review

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

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