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...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/97105 http://hdl.handle.net/10220/19649 |
| _version_ | 1826117269638348800 |
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| author | Zhang, Feng-Lian Wang, Yi-Feng Lonca, Geoffroy Hervé Zhu, Xu Chiba, Shunsuke |
| 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 |
| author_sort | Zhang, Feng-Lian |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T04:24:52Z |
| format | Journal Article |
| id | ntu-10356/97105 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:24:52Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-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. |
| 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 |
| title | 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_short | Amide synthesis by nucleophilic attack of vinyl azides |
| title_sort | amide synthesis by nucleophilic attack of vinyl azides |
| topic | DRNTU::Science::Chemistry::Inorganic chemistry::Synthesis |
| url | https://hdl.handle.net/10356/97105 http://hdl.handle.net/10220/19649 |
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