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Submillisecond organic synthesis: Outpacing Fries rearrangement throug…

Year of publication
Title of paper
Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing
Author
[김동표교수 연구실]
Publication in journal
Science, 352, pp691-694 (May 2016)
Publication date
20160506
 
[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 microreactor was applied to the synthesis of afesal, a bioactive molecule exhibiting anthelmintic activity, to demonstrate its potential for practical synthesis and production.
  
DOI: 10.1126/science.aaf1389