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

Cherif Behloul; David Guijarro; Miguel Yus

doi:10.1055/s-2004-822358

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Synthesis 2004(8): 1274-1280
DOI: 10.1055/s-2004-822358

PAPER

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
Fax: +34(96)5903549; e-Mail: yus@ua.es;

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Publikationsverlauf

Received 23 February 2004
Publikationsdatum:
03. Mai 2004 (online)

Abstract
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Abstract

The reaction of aliphatic and aromatic secondary and tertiary N-tritylamines 1 with lithium powder and a catalytic amount of naphthalene led to reductive detritylation, affording the corresponding amines 2 in good to excellent yields. The trityl group could selectively be removed in the presence of an allyl or a benzyl group. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalized N-tritylamines. The chemoselectivity between the trityl-nitrogen and the trityl-oxygen bond cleavages was also studied. This methodology represents an efficient deprotection of N-tritylamines under nonacidic reaction conditions.

Key words

tritylamine - lithium - lithiation - detritylation - reductive cleavage

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