Oligoethylene glycols as highly efficient mutifunctional promoters for nucleophilic-substitution reactions

Chemistry : a European Journal
Vinod H JadhavDong Wook Kim

Abstract

Herein, we report the promising use of n-oligoethylene glycols (oligoEGs) as mutifunctional promoters for nucleophilic-substitution reactions employing alkali metal salts. Among the various oligoEGs tested, pentaethylene glycol (pentaEG) had the most efficient catalytic activity. In particular, when compared with other nucleophiles examined, a fluorine nucleophile generated from CsF was significantly activated by the pentaEG promoter. We also performed various facile nucleophilic-displacement reactions, such as the halogenation, acetoxylation, thioacetoxylation, nitrilation, and azidation of various substrates with potassium halides, acetate, thioacetate, cyanide, and sodium azide, respectively, in the presence of the pentaEG promoter. All of these reactions provided their desired products in excellent yields. Furthermore, the combination of pentaEG and a tert-alcohol medium showed tremendous efficiency in the nucleophilic-displacement reactions (fluorination and methoxylation) of base-sensitive substrates with basic nucleophiles (cesium fluoride and potassium methoxide, respectively). The catalytic role of oligoEGs was examined by quantum-chemical methods. The oxygen atoms in oligoEGs were found to act as Lewis bases on the me...Continue Reading

References

May 24, 2003·The Journal of Organic Chemistry·Dong Wook KimDae Yoon Chi
May 13, 2004·Chemical Reviews·Mieczysław Makosza, Krzysztof Wojciechowski
Feb 17, 2005·Journal of the American Chemical Society·Haoran Sun, Stephen G DiMagno
Sep 21, 2007·The Journal of Physical Chemistry. a·Young-Ho OhSungyul Lee
Apr 1, 2010·Nuclear Medicine and Molecular Imaging·Dong Wook KimMyung-Hee Sohn

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Citations

Feb 18, 2016·Chemistry : a European Journal·Vinod H JadhavDong Wook Kim
Nov 22, 2012·Nature Communications·Hailong YanChoong Eui Song
Feb 13, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Young-Ho OhSungyul Lee
Apr 10, 2015·Chemical Reviews·Pier Alexandre ChampagneJean-François Paquin
Nov 24, 2020·The Journal of Organic Chemistry·Samuel L SilvaJosefredo R Pliego
Oct 24, 2019·The Journal of Physical Chemistry. a·Josefredo R Pliego

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