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The Role of Phase Transfer Catalysis in the Microwave-Assisted N-Benzylation of Amides, Imides and N-Heterocycles

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The effect of triethylbenzylammonium chloride (TEBAC) was studied on the outcome of the microwaveassisted solid-liquid phase N-alkylation of amides, imides and N-heterocycles using benzyl halides and K2CO3. It was found that while the benzylation of amides may be somewhat promoted by the presence of TEBAC, succinimide and benzimidazole are so reactive that there is no need to use the catalyst. At the same time, the outcome of the benzylation of phenothiazine may be significantly influenced by the presence or absence of TEBAC in respect of N- versus C-alkylation.

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Keywords: N-alkylation; microwave; phase transfer catalysis; selectivity

Document Type: Research Article

Publication date: 2009-10-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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