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超越催化剂失活:涉及含氮杂芳烃烯烃的交叉复分解反应

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics.

作者信息

Lafaye Kevin, Bosset Cyril, Nicolas Lionel, Guérinot Amandine, Cossy Janine

机构信息

Laboratoire 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, France.

出版信息

Beilstein J Org Chem. 2015 Nov 18;11:2223-41. doi: 10.3762/bjoc.11.241. eCollection 2015.

DOI:10.3762/bjoc.11.241
PMID:26664645
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4660986/
Abstract

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.

摘要

已知含有N-杂芳烃的烯烃在交叉复分解反应中是较差的反应伙伴,这可能是由于氮原子的存在导致催化剂失活。然而,文献中可以找到一些涉及含有N-杂芳烃的烯烃的关环复分解和交叉复分解的例子。此外,最近的机理研究集中在对氮诱导催化剂失活的合理化解释上。本综述的目的是简要概述涉及含有N-杂芳烃的烯烃的成功复分解反应,以便为在复分解反应中使用这些具有挑战性的底物划定一些指导原则。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/75be0f93ab86/Beilstein_J_Org_Chem-11-2223-g016.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/57c043a529d6/Beilstein_J_Org_Chem-11-2223-g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/4ee3f358de40/Beilstein_J_Org_Chem-11-2223-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/5ef774d38c55/Beilstein_J_Org_Chem-11-2223-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/75be0f93ab86/Beilstein_J_Org_Chem-11-2223-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/409b916f98f1/Beilstein_J_Org_Chem-11-2223-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/14934ba32fac/Beilstein_J_Org_Chem-11-2223-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/f40f5c0097e6/Beilstein_J_Org_Chem-11-2223-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/57c043a529d6/Beilstein_J_Org_Chem-11-2223-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/b00ab8f582e7/Beilstein_J_Org_Chem-11-2223-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/55cbea7fd60d/Beilstein_J_Org_Chem-11-2223-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/4ee3f358de40/Beilstein_J_Org_Chem-11-2223-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/5ef774d38c55/Beilstein_J_Org_Chem-11-2223-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2ff2/4660986/75be0f93ab86/Beilstein_J_Org_Chem-11-2223-g016.jpg

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