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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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Key Words

tritylamine,  lithium, lithiation, detritylation, reductive cleavage


ID: J66-Y2004-2080