Abstract
Syntheses and applications of new bis-piperidinium and bis-pyrrolidinium compounds as effective two-center phase-transfer catalysts are presented. Applications of these catalysts have been explored in etherification and N-alkylation reactions, and comparisons between these catalysts and traditional phase-transfer catalysts such as cetyltrimethylammonium bromide (CTAB) and 1-ethyl-3-methylimidazolium chloride (emim + Cl - ) are presented.
Highlights
Phase-transfer catalysis (PTC) has been proved as a practical methodology in organic synthesis due to its simplicity, mild reaction conditions, better yields, and safer environmental protocols.[1]
The synthesis of bis-piperidinium compounds 1a-1l was carried out by amination of p-xylylene dibromide with two equivalents of piperidine followed by quaternization with alkyl bromides or iodides to produce the bis-quaternary compounds in good yields. (Scheme 1)
The bis-pyrrolidinium compounds 2a-2l were prepared in a similar way by amination of p-xylylene dibromide with two equivalents of pyrrolidine followed by quaternization with alkyl bromides or iodides. (Scheme 2)
Summary
Phase-transfer catalysis (PTC) has been proved as a practical methodology in organic synthesis due to its simplicity, mild reaction conditions, better yields, and safer environmental protocols.[1]. These advantages make bis-quaternary ammonium compounds qualify as phase-transfer catalysts in alkylations and other reactions.
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