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Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts
Author(s) -
Kulchat Sirinan,
Lehn JeanMarie
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500604
Subject(s) - chemistry , pyridinium , nucleophilic substitution , nucleophile , pyridine , iodide , ammonium , ionic bonding , ionic liquid , organic chemistry , medicinal chemistry , inorganic chemistry , catalysis , ion
Dynamic covalent libraries (DCLs) of quaternary ammonium cations were set up by reversible nucleophilic substitution (S N 2′ and S N 2) exchange reactions of ammonium salts and tertiary amines. The reactions were conducted at 60 °C to generate thermodynamically and kinetically controlled mixtures of quaternary ammonium compounds and tertiary amines, and were accelerated by using iodide as a nucleophilic catalyst. Microwave irradiation was used to assist the exchange reaction between the pyridinium salts and pyridine derivatives. Finally, experiments towards the generation of dynamic ionic liquids were performed. The results of this study pave the way for the extension of dynamic combinatorial chemistry to nucleophilic substitution reactions.