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Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion

Smallman, Harry R; Brancaglion, Guilherme A; Pastre, Julio C; Browne, Duncan L; (2022) Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion. The Journal of Organic Chemistry 10.1021/acs.joc.2c01486. (In press). Green open access

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Abstract

A flow chemistry process for the generation and use of acylketene precursors through extrusion of nitrogen gas is reported. Key to the development of a suitable continuous protocol is the balance of reaction concentration against pressure in the flow reactor. The resulting process enables access to intercepted acylketene scaffolds using volatile amine nucleophiles and has been demonstrated on the gram scale. Thermal gravimetric analysis was used to guide the temperature set point of the reactor coils for a variety of acyl ketene precursors. The simultaneous generation and reaction of two reactive intermediates (both derived from nitrogen extrusion) is demonstrated.

Type: Article
Title: Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.joc.2c01486
Publisher version: https://doi.org/10.1021/acs.joc.2c01486
Language: English
Additional information: This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third-party material in this article are included in the Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
UCL classification: UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
URI: https://discovery.ucl.ac.uk/id/eprint/10155179
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