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Accelerating Palladium-Catalyzed C[BOND]F Bond Formation: Use of a Microflow Packed-Bed Reactor

Authors


  • T.N., T.J.M., and S.L.B. thank the Novartis International AG and the National Institutes of Health (Grant GM46059) for financial support of this work. T.N. is a Fulbright Postdoctoral Fellow. T.J.M. thanks the NIH for a postdoctoral fellowship (1F32GM088931). The Varian 300 MHz NMR spectrometer used for portions of this work was purchased with funds from the National Science Foundation (Grants CHE 9808061 and DBI 9729592). The authors would like to acknowledge Dr. Simon Kuhn for helpful and stimulating discussions as well as assistance in particle size distribution measurements.

Abstract

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A flow process for Pd-catalyzed C[BOND]F bond formation is described. A microreactor with a packed-bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted into aryl fluorides in short reaction times (see scheme).

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