Altering Product Selectivity by Mechanochemistry

Mechanochemical activation achieved by grinding, shearing, pulling, or milling opens unique opportunities in synthetic organic chemistry. Common features are that mechanochemistry facilitates reactions with insoluble reactants, enables high-yielding solvent-free synthetic procedures, and shortens re...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-04, Vol.82 (8), p.4007-4019
Main Authors: Hernández, José G, Bolm, Carsten
Format: Article
Language:English
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Summary:Mechanochemical activation achieved by grinding, shearing, pulling, or milling opens unique opportunities in synthetic organic chemistry. Common features are that mechanochemistry facilitates reactions with insoluble reactants, enables high-yielding solvent-free synthetic procedures, and shortens reaction times, among others. However, mechanochemical techniques can also alter chemical reactivity and selectivity compared to the analogous solution-based protocols. As a consequence, solvent-free milling can lead to different product compositions or equilibration mixtures than in solution. Reactions by milling have also allowed the trapping and characterization of elusive intermediates and materials. In this Perspective we highlight a few selected examples that illustrate the value of mechanochemistry in uncovering interesting chemical reactivity, which is often masked in typical liquid-phase synthesis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02887