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Synlett 2011(9): 1251-1254  
DOI: 10.1055/s-0030-1260539
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© Georg Thieme Verlag Stuttgart ˙ New York

Brønsted Acid Catalyzed Reductive Amination with Benzothiazoline as a Highly Efficient Hydrogen Donor

Chen Zhu, Takahiko Akiyama*
Department of Chemistry, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
Fax: +81(3)59921029; e-Mail: takahiko.akiyama@gakushuin.ac.jp;
Further Information

Publication History

Received 7 February 2011
Publication Date:
20 April 2011 (online)

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Abstract

Reductive amination of aldehyde and amine proceeded smoothly in the presence of benzothiazoline as efficient hydrogen source by means of 20 mol% trifluoroacetic acid to give the corresponding amines in excellent yields. Hydrogen-donor abilities of benzothiazoline, benzimidazoline, and benzoxazoline were compared.

Key words

reduction - reductive amination - benzothiazoline - transfer hydrogenation - phosphoric acid

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16

Aliphatic amines such as benzylamine and n-pentylamine did not give the reduction products.

17

The reactions were performed with 20 mol% TFA in CH2Cl2 at 0.07 M concentration.