Sensitized [2 + 2] intramolecular photocycloaddition of unsaturated enones using UV LEDs in a continuous flow reactor: kinetic and preparative aspects
- Resource Type
- Authors
- Laëtitia Chausset-Boissarie; Youssef Bakkour; Christian Rolando; Maël Penhoat; Nassim El Achi; Fabien Gelat; Ahmed Mazzah; Nicolas P. Cheval
- Source
- Reaction Chemistry & Engineering
Reaction Chemistry & Engineering, 2019, 4 (5), pp.828-837. ⟨10.1039/C8RE00314A⟩
Reaction Chemistry & Engineering, Royal Society of Chemistry, 2019, 4 (5), pp.828-837. ⟨10.1039/C8RE00314A⟩
- Subject
- Fluid Flow and Transfer Processes
Materials science
Order of reaction
010405 organic chemistry
Pinacol
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Process Chemistry and Technology
Batch reactor
Flow chemistry
010402 general chemistry
Photochemistry
7. Clean energy
01 natural sciences
Catalysis
0104 chemical sciences
Cyclobutane
chemistry.chemical_compound
chemistry
Chemistry (miscellaneous)
Intramolecular force
Ionic liquid
Chemical Engineering (miscellaneous)
[CHIM]Chemical Sciences
Microreactor
ComputingMilieux_MISCELLANEOUS
- Language
- English
- ISSN
- 2058-9883
A catalytically sensitized intramolecular [2 + 2] photocycloaddition reaction of 3-alkenyloxy-2-cycloalkenones onto cyclobutanes was studied using a flow microreactor irradiated by high power UV-A LEDs. During the course of the study we also identified an ionic liquid photosensitizer that facilitates the purification of the photocycloaddition product. Good to excellent yields were obtained in flow for a variety of substrates by applying significantly shorter residence times than those needed in a conventional batch reactor. The flow device enabled the determination of highly accurate kinetic data which supported a second order reaction rate in the substrate and photocatalyst for the [2 + 2] photocycloaddition reaction and a first order in the photocatalyst for the pinacolisation of the sensitizer. Furthermore, the kinetic model and flow chemistry data enabled us to obtain excellent fits for both cyclobutane and pinacol even at almost full conversions.