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. 2019 Mar 4;9(13):7203-7209.
doi: 10.1039/c9ra00616h. eCollection 2019 Mar 1.

Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination

Dianke Xie  1 , Wei He  1 , Jiang Xiao  1 , Yao Wu  1 , Yongjia Guo  1 , Qiang Liu  1 , Cancheng Guo  1
Affiliations

Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp3)-H amidination

Dianke Xie et al. RSC Adv. .

Abstract

A convenient method for the synthesis of 2-oxo-acetamidines from methyl ketones using aromatic amines and DMF as nitrogen sources is reported via copper-catalyzed C(sp3)-H amidination. Various methyl ketones react readily with aromatic amines and DMF, producing 2-oxo-acetamidines in yields of 47 to 92%. This protocol features the simultaneous formation of C-N and C[double bond, length as m-dash]N bonds using DMF and aromatic amines as two different nitrogen sources. It thus provides an efficient approach to construct acyclic amidines via three C(sp3)-H bond amidination. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

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Conflict of interest statement

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Figures

Scheme 1
Scheme 1. Methods for the synthesis of amidines.
Scheme 2
Scheme 2. Different control experiments.
Scheme 3
Scheme 3. A proposed mechanism for the direct transformation.
See this image and copyright information in PMC

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