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Detritylation of N-Tritylamines via a Naphthalene-Catalyzed Lithiation Process

Cherif Behloul, David Guijarro, Miguel Yus*

*Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Email: yusua.es

C. Behloul, D. Guijarro, M. Yus, Synthesis, 2004, 1274-1280.

DOI: 10.1055/s-2004-822358


Abstract

The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines with lithium powder and a catalytic amount of naphthalene led to reductive detritylation affording the corresponding amines in good yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group.

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Details

The document discusses a method for the detritylation of N-tritylamines using a naphthalene-catalyzed lithiation process. This method involves the reaction of aliphatic and aromatic secondary and tertiary N-tritylamines with lithium powder and a catalytic amount of naphthalene, resulting in the reductive removal of the trityl group and yielding the corresponding amines in good to excellent yields. The process is selective, allowing the trityl group to be removed in the presence of allyl or benzyl groups. The methodology is effective for various functionalized N-tritylamines, including those with hydroxy, alkoxy, and amino groups. The study also explores the chemoselectivity between trityl-nitrogen and trityl-oxygen bond cleavages. The optimal reaction conditions were found to be at 0 °C, providing high yields. This method offers an efficient, non-acidic alternative for the deprotection of N-tritylamines, which is particularly useful in peptide and cephalosporin synthesis. The document includes detailed experimental procedures, results, and analysis, highlighting the advantages of this lithiation process over traditional acidic or metal-catalyzed detritylation methods.


Key Words

tritylamine, lithium, lithiation, detritylation, reductive cleavage


ID: J66-Y2004-2080