Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion

Author(s)

Smallman, Harry R. ; Brancaglion, Guilherme A. ; Pastre, Julio C. ; Browne, Duncan L.

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 87, n. 18, p. 9-pg., 2022-09-01.

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. (AU)

• FAPESP's process: 21/06661-5 - Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Young Investigators Grants - Phase 2