2008•Letters in Organic ChemistryRequires access

Reductive Amination of Aldehydes and Ketones with Xylylene Ionene Bound Borohydride as a Novel Polymer Supported Reducing Agent

Mahmood Tajbakhsh, Moslem Mansour Lakouraj, Majid Shabani Mahalli

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Abstract

An efficient reductive amination of aldehydes and ketones in the preparation of aliphatic and aromatic secondary and tertiary amines with xylylene ionene borohydride as a high capacity polymer supported reducing agent in isopropanol at reflux under neutral conditions is described. Xylylene ionene borohydride is easily prepared by mixing an aqueous solution of xylylene ionene chloride with an alkaline solution of sodium borohydride at room temperature. The chemoselective reductive amination in the presence of functional groups such as chloride, C=C bond, nitro and cyano groups was also achieved. The generality of reaction was established using variety of aldehydes, ketones and amines. Keywords: Ionene borohydride, reductive amination, aldehyde, ketone

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An efficient reductive amination of aldehydes and ketones in the preparation of aliphatic and aromatic secondary and tertiary amines with xylylene ionene borohydride as a high capacity polymer supported reducing agent in isopropanol at reflux under neutral conditions is described. Xylylene ionene borohydride is easily prepared by mixing an aqueous solution of xylylene ionene chloride with an alkaline solution of sodium borohydride at room temperature. The chemoselective reductive amination in the presence of functional groups such as chloride, C=C bond, nitro and cyano groups was also achieved. The generality of reaction was established using variety of aldehydes, ketones and amines. Keywords: Ionene borohydride, reductive amination, aldehyde, ketone

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Available abstract

An efficient reductive amination of aldehydes and ketones in the preparation of aliphatic and aromatic secondary and tertiary amines with xylylene ionene borohydride as a high capacity polymer supported reducing agent in isopropanol at reflux under neutral conditions is described. Xylylene ionene borohydride is easily prepared by mixing an aqueous solution of xylylene ionene chloride with an alkaline solution of sodium borohydride at room temperature. The chemoselective reductive amination in the presence of functional groups such as chloride, C=C bond, nitro and cyano groups was also achieved. The generality of reaction was established using variety of aldehydes, ketones and amines. Keywords: Ionene borohydride, reductive amination, aldehyde, ketone

Key concepts: Reductive amination, Chemistry, Sodium borohydride, Borohydride, Sodium cyanoborohydride, Reducing agent, Xylylene, Amination

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Reductive Amination of Aldehydes and Ketones with Xylylene Ionene Bound Borohydride as a Novel Polymer Supported Reducing Agent — Research Paper | ScholarLens