Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics
Alkenes containing N-heteroaromatics are known to be poor partners in cross-metathesis reactions, probably due to catalyst deactivation caused by the presence of a nitrogen atom. However, some examples of ring-closing and cross-metathesis involving alkenes that incorporate N-heteroaromatics can be f...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.241 |
| _version_ | 1818933722741735424 |
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| author | Kevin Lafaye Cyril Bosset Lionel Nicolas Amandine Guérinot Janine Cossy |
| author_facet | Kevin Lafaye Cyril Bosset Lionel Nicolas Amandine Guérinot Janine Cossy |
| author_sort | Kevin Lafaye |
| collection | DOAJ |
| description | Alkenes containing N-heteroaromatics are known to be poor partners in cross-metathesis reactions, probably due to catalyst deactivation caused by the presence of a nitrogen atom. However, some examples of ring-closing and cross-metathesis involving alkenes that incorporate N-heteroaromatics can be found in the literature. In addition, recent mechanistic studies have focused on the rationalization of nitrogen-induced catalysts deactivation. The purpose of this mini-review is to give a brief overview of successful metathesis reactions involving olefins containing N-heteroaromatics in order to delineate some guidelines for the use of these challenging substrates in metathesis reactions. |
| first_indexed | 2024-12-20T04:52:54Z |
| format | Article |
| id | doaj.art-56b234890e824051b90992172c3fc187 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T04:52:54Z |
| publishDate | 2015-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-56b234890e824051b90992172c3fc1872022-12-21T19:52:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-11-011112223224110.3762/bjoc.11.2411860-5397-11-241Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromaticsKevin Lafaye0Cyril Bosset1Lionel Nicolas2Amandine Guérinot3Janine Cossy4Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, FranceLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, FranceLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, FranceLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, FranceLaboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI ParisTech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, FranceAlkenes containing N-heteroaromatics are known to be poor partners in cross-metathesis reactions, probably due to catalyst deactivation caused by the presence of a nitrogen atom. However, some examples of ring-closing and cross-metathesis involving alkenes that incorporate N-heteroaromatics can be found in the literature. In addition, recent mechanistic studies have focused on the rationalization of nitrogen-induced catalysts deactivation. The purpose of this mini-review is to give a brief overview of successful metathesis reactions involving olefins containing N-heteroaromatics in order to delineate some guidelines for the use of these challenging substrates in metathesis reactions.https://doi.org/10.3762/bjoc.11.241catalyst deactivationcross-metathesisN-heteroaromaticpyridinering-closing metathesis |
| spellingShingle | Kevin Lafaye Cyril Bosset Lionel Nicolas Amandine Guérinot Janine Cossy Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics Beilstein Journal of Organic Chemistry catalyst deactivation cross-metathesis N-heteroaromatic pyridine ring-closing metathesis |
| title | Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics |
| title_full | Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics |
| title_fullStr | Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics |
| title_full_unstemmed | Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics |
| title_short | Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics |
| title_sort | beyond catalyst deactivation cross metathesis involving olefins containing n heteroaromatics |
| topic | catalyst deactivation cross-metathesis N-heteroaromatic pyridine ring-closing metathesis |
| url | https://doi.org/10.3762/bjoc.11.241 |
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