Development of a Continuous Photochemical Benzyne-Forming Process

• Cormac Bracken^a
• Andrei S. Batsanov^b
• Marcus Baumann^a

• ^aSchool of Chemistry, University College Dublin, Science Centre South, D04 N2E2, Dublin, Ireland
• ^bDepartment of Chemistry, University of Durham, South Road, DH1 3LE, Durham, UK

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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