PAPER	Synthesis 2004: 1274-1280   DOI: 10.1055/s-2004-822358
© Georg Thieme Verlag Stuttgart · New York
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;
Received 23 February 2004

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