Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination

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(sp(3))–H amidination. Various methyl ketones react readily with aromatic amines and DMF, producing 2-oxo-acetamidines in yields of 47 t...

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Detalles Bibliográficos
Autores principales: Xie, Dianke, He, Wei, Xiao, Jiang, Wu, Yao, Guo, Yongjia, Liu, Qiang, Guo, Cancheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9061129/
https://www.ncbi.nlm.nih.gov/pubmed/35519951
http://dx.doi.org/10.1039/c9ra00616h
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author Xie, Dianke
He, Wei
Xiao, Jiang
Wu, Yao
Guo, Yongjia
Liu, Qiang
Guo, Cancheng
author_facet Xie, Dianke
He, Wei
Xiao, Jiang
Wu, Yao
Guo, Yongjia
Liu, Qiang
Guo, Cancheng
author_sort Xie, Dianke
collection PubMed
description 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(sp(3))–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(sp(3))–H bond amidination. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
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spelling pubmed-90611292022-05-04 Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination Xie, Dianke He, Wei Xiao, Jiang Wu, Yao Guo, Yongjia Liu, Qiang Guo, Cancheng RSC Adv Chemistry 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(sp(3))–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(sp(3))–H bond amidination. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed. The Royal Society of Chemistry 2019-03-04 /pmc/articles/PMC9061129/ /pubmed/35519951 http://dx.doi.org/10.1039/c9ra00616h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Xie, Dianke
He, Wei
Xiao, Jiang
Wu, Yao
Guo, Yongjia
Liu, Qiang
Guo, Cancheng
Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title_full Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title_fullStr Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title_full_unstemmed Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title_short Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination
title_sort direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and dmf via copper-catalyzed c(sp(3))–h amidination
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9061129/
https://www.ncbi.nlm.nih.gov/pubmed/35519951
http://dx.doi.org/10.1039/c9ra00616h
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