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 journalArticle

108 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

ASJC Scopus subject areas

  • General

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