Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon–carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a un...

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Detalles Bibliográficos
Autores principales: Liu, Wei-Bing, Chen, Cui, Zhang, Qing, Zhu, Zhi-Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326611/
https://www.ncbi.nlm.nih.gov/pubmed/22509203
http://dx.doi.org/10.3762/bjoc.8.38
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author Liu, Wei-Bing
Chen, Cui
Zhang, Qing
Zhu, Zhi-Bo
author_facet Liu, Wei-Bing
Chen, Cui
Zhang, Qing
Zhu, Zhi-Bo
author_sort Liu, Wei-Bing
collection PubMed
description A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon–carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides.
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spelling pubmed-33266112012-04-16 Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides Liu, Wei-Bing Chen, Cui Zhang, Qing Zhu, Zhi-Bo Beilstein J Org Chem Full Research Paper A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon–carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides. Beilstein-Institut 2012-03-07 /pmc/articles/PMC3326611/ /pubmed/22509203 http://dx.doi.org/10.3762/bjoc.8.38 Text en Copyright © 2012, Liu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Liu, Wei-Bing
Chen, Cui
Zhang, Qing
Zhu, Zhi-Bo
Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title_full Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title_fullStr Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title_full_unstemmed Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title_short Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides
title_sort organic synthesis using (diacetoxyiodo)benzene (dib): unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-n-phenylacetamides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326611/
https://www.ncbi.nlm.nih.gov/pubmed/22509203
http://dx.doi.org/10.3762/bjoc.8.38
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