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1-甲基环丙基甲醛和2,2,2-三氟苯乙酮对杂环卡宾有机催化剂的意外失活

An Unexpected Inactivation of -Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone.

作者信息

Chen Yanling, Lv Jie, Pan Xuling, Jin Zhichao

机构信息

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China.

出版信息

Front Chem. 2022 Mar 24;10:875286. doi: 10.3389/fchem.2022.875286. eCollection 2022.

DOI:10.3389/fchem.2022.875286
PMID:35402372
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8988059/
Abstract

An unprecedented inactivation process of the indanol-derived NHC catalysts bearing -CF groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The absolute structure of the inactivation product is unambiguously assigned X-ray analysis on its single crystals. The formation of the structurally complex product is rationalized through a multi-step cascade cyclization process.

摘要

报道了一种前所未有的带有-CF基团的茚满醇衍生的NHC催化剂的失活过程。在与1-甲基环丙基甲醛、2,2,2-三氟苯乙酮和NHC催化剂的三组分反应中得到了一种意想不到的多环络合物产物。通过对其单晶进行X射线分析，明确确定了失活产物的绝对结构。通过多步级联环化过程对结构复杂产物的形成进行了合理的解释。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/128d161d3363/fchem-10-875286-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/1d9f5ca29008/fchem-10-875286-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/c42e82ab62c6/fchem-10-875286-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/128d161d3363/fchem-10-875286-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/1d9f5ca29008/fchem-10-875286-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/c42e82ab62c6/fchem-10-875286-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ff3/8988059/128d161d3363/fchem-10-875286-g003.jpg

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Chemistry. 2021 Feb 5;27(8):2662-2669. doi: 10.1002/chem.202003454. Epub 2020 Dec 1.
2
N-Heterocyclic Carbenes as Key Intermediates in the Synthesis of Fused, Mesoionic, Tricyclic Heterocycles.N-杂环卡宾作为稠合、介离子、三环杂环合成中的关键中间体。
Chemistry. 2019 Oct 8;25(56):13030-13036. doi: 10.1002/chem.201903242. Epub 2019 Sep 9.
3
A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of γ-butyrolactones.
持续的挑战：N-杂环卡宾催化γ-丁内酯合成。
Chem Soc Rev. 2018 Mar 5;47(5):1773-1782. doi: 10.1039/c7cs00386b.
4
Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols azolium enolates, and the characterization of advanced reaction intermediates.卡宾催化α,β-烯醛的极性反转：二氨基二烯醇、唑鎓烯醇盐的反应活性研究及高级反应中间体的表征
Chem Sci. 2015 Jul 15;6(7):3706-3711. doi: 10.1039/c5sc01027f. Epub 2015 Apr 30.
5
Recent advances in employing homoenolates generated by N-heterocyclic carbene (NHC) catalysis in carbon-carbon bond-forming reactions.N-杂环卡宾（NHC）催化生成的偕烯醇盐在碳-碳键形成反应中的应用的最新进展。
Chem Soc Rev. 2015 Aug 7;44(15):5040-52. doi: 10.1039/c5cs00162e. Epub 2015 May 27.
6
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.氮杂环卡宾催化的有机反应
Chem Rev. 2015 Sep 9;115(17):9307-87. doi: 10.1021/acs.chemrev.5b00060. Epub 2015 May 20.
7
An overview of N-heterocyclic carbenes.N-杂环卡宾综述。
Nature. 2014 Jun 26;510(7506):485-96. doi: 10.1038/nature13384.
8
On the mechanism of N-heterocyclic carbene-catalyzed reactions involving acyl azoliums.N-杂环卡宾催化的酰基唑鎓反应的机理。
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9
SAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.涉及五氟苯基三唑鎓卡宾的源自SAr的分解副产物。
Synlett. 2013 Jun 17;24(10). doi: 10.1055/s-0033-1338842.
10
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Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11158-62. doi: 10.1002/anie.201303107. Epub 2013 Aug 28.