Journal
SYNOPEN
Volume 5, Issue 1, Pages 29-35Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706016
Keywords
flow chemistry; photochemistry; benzyne; cycloadditions; high-energy intermediates; reaction development; heterocycles
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Funding
- SSPC (European Regional Development Fund) [12/RC2275_P2]
- Science Foundation Ireland Infrastructure Call 2018 [18/RI/5702]
- School of Chemistry at UCD
- RSC Research Enablement Grant [E20-2998]
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A new methodology utilizing a high-power LED lamp for the safe generation and derivatization of benzyne under photochemical conditions is presented. The continuous-flow process effectively controls the release of gaseous by-products and delivers a series of heterocyclic products in a short residence time. This robust methodology enables the rapid generation of important heterocyclic scaffolds through a simple and scalable flow protocol.
A continuous-flow process is presented that enables the safe generation and derivatization of benzyne under photochemical conditions. This is facilitated by a new high-power LED lamp emitting light at 365 nm. The resulting flow process effectively controls the release of gaseous by-products based on an adjustable backpressure regulator and delivers a series of heterocyclic products in a short residence time of 3 minutes. The robustness of this methodology is demonstrated for the rapid generation of benzotriazoles, 2H-indazoles and various furan-derived adducts, facilitating the preparation of these important heterocyclic scaffolds via a simple and readily scalable flow protocol.
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