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[Report] Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing

ScienceNOW - Fetched: May 5th, 2016, 4:00pm UTC

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 microreactor was applied to the synthesis of afesal, a bioactive molecule exhibiting anthelmintic activity, to demonstrate its potential for practical synthesis and production. Authors: Heejin Kim, Kyoung-Ik Min, Keita Inoue, Do Jin Im, Dong-Pyo Kim, Jun-ichi Yoshida

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