Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction

Jean-Baptiste Gualtierotti; Xavier Schumacher; Qian Wang; Jieping Zhu

doi:10.1055/s-0032-1316908

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1380-1386
DOI: 10.1055/s-0032-1316908

paper

Synthesis of Iminonitriles by Oxone/TBAB-Mediated One-Pot Oxidative Three-Component Strecker Reaction

Jean-Baptiste Gualtierotti

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 Email: jieping.zhu@epfl.ch

,

Xavier Schumacher

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 Email: jieping.zhu@epfl.ch

,

Qian Wang

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 Email: jieping.zhu@epfl.ch

,

Jieping Zhu*

Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland Fax: +41(21)6939740 Email: jieping.zhu@epfl.ch

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Abstract

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Abstract

Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H₂O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using α,β-unsaturated aldehydes as inputs.

Key words

α-iminonitrile - Oxone - α-aminonitrile - oxidative three-component Strecker reaction - multicomponent reaction

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References

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