Exploring the generation and use of acylketenes with continuous flow processes

Author(s)

Galaverna, Renan ^{[1, 2]} ; McBride, Tom ^[2] ; Pastre, Julio C. ^[1] ; Browne, Duncan L. ^[2]

Affiliation

^[1] Univ Campinas UNICAMP, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

^[2] Cardiff Univ, Sch Chem, Main Bldg, Pk Pl, Cardiff CF10 3AT, S Glam - Wales

• Document type: Journal article
• Source: REACTION CHEMISTRY & ENGINEERING; v. 4, n. 9, p. 1559-1564, SEP 1 2019.
• Web of Science Citations: 0

Abstract

The generation and use of reactive intermediates is well suited to continuous flow processing owing to the ability to scale up reactions, contain hazards and heat solvents past their atmospheric temperature boiling points. Herein we explore the chemistry of acylketenes, generated from commercially available 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 10) under continuous flow conditions. The developed flow chemistry system is capable of permitting a wide range of applications of these acylketene intermediates, including access to equilibrating processes that result in ketone exchange. Some of the dioxinone products resulting from this study are destabilised towards acylketene generation, this is demonstrated through their ability to generate acylketene at lower reaction temperatures. (AU)

• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Research Grants - Young Investigators Grants