Amide synthesis by nucleophilic attack of vinyl azides

A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3⋅OEt2. After nucleophilic attack of the vinyl azi...

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Main Authors:	Zhang, Feng-Lian, Wang, Yi-Feng, Lonca, Geoffroy Hervé, Zhu, Xu, Chiba, Shunsuke
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2014
Subjects:	DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis
Online Access:	https://hdl.handle.net/10356/97105 http://hdl.handle.net/10220/19649
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Institution:	Nanyang Technological University
Language:	English

id	sg-ntu-dr.10356-97105
record_format	dspace
spelling	sg-ntu-dr.10356-971052020-03-07T12:34:40Z Amide synthesis by nucleophilic attack of vinyl azides Zhang, Feng-Lian Wang, Yi-Feng Lonca, Geoffroy Hervé Zhu, Xu Chiba, Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3⋅OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide. 2014-06-11T03:09:39Z 2019-12-06T19:38:59Z 2014-06-11T03:09:39Z 2019-12-06T19:38:59Z 2014 2014 Journal Article Zhang, F.-L., Wang, Y.-F., Lonca, G. H., Zhu, X., & Chiba, S. (2014). Amide Synthesis by Nucleophilic Attack of Vinyl Azides. Angewandte Chemie International Edition, 53(17), 4390-4394. 1433-7851 https://hdl.handle.net/10356/97105 http://hdl.handle.net/10220/19649 10.1002/anie.201400938 en Angewandte chemie international edition © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution	Nanyang Technological University
building	NTU Library
country	Singapore
collection	DR-NTU
language	English
topic	DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis
spellingShingle	DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis Zhang, Feng-Lian Wang, Yi-Feng Lonca, Geoffroy Hervé Zhu, Xu Chiba, Shunsuke Amide synthesis by nucleophilic attack of vinyl azides
description	A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3⋅OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Zhang, Feng-Lian Wang, Yi-Feng Lonca, Geoffroy Hervé Zhu, Xu Chiba, Shunsuke
format	Article
author	Zhang, Feng-Lian Wang, Yi-Feng Lonca, Geoffroy Hervé Zhu, Xu Chiba, Shunsuke
author_sort	Zhang, Feng-Lian
title	Amide synthesis by nucleophilic attack of vinyl azides
title_short	Amide synthesis by nucleophilic attack of vinyl azides
title_full	Amide synthesis by nucleophilic attack of vinyl azides
title_fullStr	Amide synthesis by nucleophilic attack of vinyl azides
title_full_unstemmed	Amide synthesis by nucleophilic attack of vinyl azides
title_sort	amide synthesis by nucleophilic attack of vinyl azides
publishDate	2014
url	https://hdl.handle.net/10356/97105 http://hdl.handle.net/10220/19649
_version_	1681039022583971840

Amide synthesis by nucleophilic attack of vinyl azides

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