Journal
SCIENCE
Volume 352, Issue 6286, Pages 691-694Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaf1389
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Funding
- National Research Foundation of Korea [2008-0061983, NRF-2015R1D1A3A01019112, NRF-2014M1A8A1074940]
- Japan Society for the Promotion of Science [26220804]
- National Research Foundation of Korea [2014M1A8A1074940, 2008-0061983] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- Grants-in-Aid for Scientific Research [16K17898, 26220804] Funding Source: KAKEN
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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.
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