Liquid-assisted grinding and ion pairing regulates percentage conversion and diastereoselectivity of the Wittig reaction under mechanochemical conditions

Mechanochemistry is maturing as a discipline and continuing to grow, so it is important to continue understanding the rules governing the system. In a mechanochemical reaction, the reactants are added into a vessel along with one or more grinding balls and the vessel is shaken at high speeds to faci...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018-03, Vol.14 (1), p.688-696
Main Authors: Denlinger, Kendra Leahy, Ortiz-Trankina, Lianna, Carr, Preston, Benson, Kingsley, Waddell, Daniel C, Mack, James
Format: Article
Language:English
Subjects:
Chemistry
Dielectric constant
Ethanol
Evaporation
Full Research Paper
green chemistry
high-speed ball milling
HSBM
LAG
liquid-assisted grinding
Solvents
Stainless steel
Wittig
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Summary:Mechanochemistry is maturing as a discipline and continuing to grow, so it is important to continue understanding the rules governing the system. In a mechanochemical reaction, the reactants are added into a vessel along with one or more grinding balls and the vessel is shaken at high speeds to facilitate a chemical reaction. The dielectric constant of the solvent used in liquid-assisted grinding (LAG) and properly chosen counter-ion pairing increases the percentage conversion of stilbenes in a mechanochemical Wittig reaction. Utilizing stepwise addition/evaporation of ethanol in liquid-assisted grinding also allows for the tuning of the diastereoselectivity in the Wittig reaction.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.14.57