In chemical synthesis, rapid intramolecular rearrangements often foil attempts at site-selective bimolecular functionalization.We developed a microfluidic technique that outpaces the very rapid anionic Fries rearrangement to chemoselectively functionalize iodophenyl carbamates at the ortho position. Central to the technique is a chip microreactor of our design, which can deliver a reaction time in the submillisecond range even at cryogenic temperatures.The microreactorwas applied to the synthesis of afesal, a bioactive molecule exhibiting anthelmintic activity, to demonstrate its potential for practical synthesis and production.
Bibliographical noteFunding Information:
Supported by National Research Foundation of Korea grants 2008-0061983, NRF-2015R1D1A3A01019112, and NRF-2014M1A8A1074940 and by Japan Society for the Promotion of Science Grant-in-Aid for Scientific Research (S) 26220804. Author contributions: H.K. and K.-I.M. conceived the concept at POSTECH; K.-I.M. fabricated the device; H.K. conducted synthetic experiments at POSETCH and Kyoto University with K.I.; D.J.I. conducted CFD simulation and analysis with K.-I.M.; and D.-P.K. and J.Y. directed the project.
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