Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing

Heejin Kim, Kyoung Ik Min, Keita Inoue, Do Jin Im, Dong Pyo Kim, Jun Ichi Yoshida

Research output: Contribution to journalArticlepeer-review

195 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)691-694
Number of pages4
JournalScience
Volume352
Issue number6286
DOIs
Publication statusPublished - 2016 May 6
Externally publishedYes

Bibliographical note

Funding 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.

ASJC Scopus subject areas

  • General

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