2016
DOI: 10.1126/science.aaf1389
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Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing

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,… Show more

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Cited by 228 publications
(145 citation statements)
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and fine chemical industries. [7][8][9][10][11] Fused silica is one of the widely used substrates for the microfluidic technology in laboratory research and industrial applications due to its high melting point, high chemical stability, low thermal expansion coefficient, wide transmission spectral range, and good biocompatibility. In particular, extension of the microfluidic networks from widely used 2D to 3D configurations has now been considered as a promising scheme to enhance the performance of manipulation of fluids such as high-efficiency mixing, separation, and detection.

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mentioning
confidence: 99%
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and fine chemical industries. [7][8][9][10][11] Fused silica is one of the widely used substrates for the microfluidic technology in laboratory research and industrial applications due to its high melting point, high chemical stability, low thermal expansion coefficient, wide transmission spectral range, and good biocompatibility. In particular, extension of the microfluidic networks from widely used 2D to 3D configurations has now been considered as a promising scheme to enhance the performance of manipulation of fluids such as high-efficiency mixing, separation, and detection.

…”
mentioning
confidence: 99%
“…Yoshida and Kim recently provided an astonishing example on the potential of flash chemistry in controlling fast isomerization of organolithiums [48]. The authors designed a chip microreactor (CMR), able to deliver a reaction time in the range of submilliseconds (0.33 ms) under cryogenic conditions.…”
Section: Reviewmentioning
confidence: 99%
“…With environmental concerns and health issues mounting, the next logical step is miniaturization of chemical reactions. [17][18][19] Heterogeneous reactions can run more efficiently in microfluidic format due to the large surface-tovolume ratios that ensure improved phase contact and heating is much easier controllable on the microscale which significantly enhances the yield of temperature-sensitive reactions. Although microreactor technology is a field which has seen significant scientific interest over the years, application demonstration has mostly been limited by the lack of suitable materials for chemical applications.…”
Section: Introductionmentioning
confidence: 99%