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

Autor: Kendra Leahy Denlinger, Lianna Ortiz-Trankina, Preston Carr, Kingsley Benson, Daniel C. Waddell, James Mack
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 688-696 (2018)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.14.57
Popis: 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.
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