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氧化膦促进的铑(I)催化苯并咪唑与烯烃的 C-H 环化反应。

Phosphine Oxide-Promoted Rh(I)-Catalyzed C-H Cyclization of Benzimidazoles with Alkenes.

机构信息

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Frontiers Science Center for New Organic Matter, Tianjin 300071, China.

Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, China.

出版信息

Molecules. 2023 Jan 11;28(2):736. doi: 10.3390/molecules28020736.

Abstract

Ligands play a critical role in promoting transition-metal-catalyzed C-H activation reactions. However, owing to high sensitivity of the reactivity of C-H activation to metal catalysts, the development of effective ligands has been a formidable challenge in the field. Rh(I)-catalyzed C-H cyclization of benzimidazoles with alkenes has been faced with low reactivity, often requiring very harsh conditions. To address this challenge, a phosphine oxide-enabled Rh(I)-Al bimetallic catalyst was developed for the reaction, significantly promoting the reactivity and allowing the reaction to run at 120 °C with up to 97% yield.

摘要

配体在促进过渡金属催化的 C-H 活化反应中起着关键作用。然而,由于 C-H 活化的反应性对金属催化剂非常敏感,因此开发有效的配体一直是该领域的一个巨大挑战。铑(I)催化的苯并咪唑与烯烃的 C-H 环化反应活性较低,通常需要非常苛刻的条件。为了解决这一挑战,开发了一种磷氧化物辅助的 Rh(I)-Al 双金属催化剂用于该反应,显著提高了反应活性,使反应在 120°C 下进行,产率高达 97%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fa51/9864171/345213f5e0c5/molecules-28-00736-sch001.jpg

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本文引用的文献

1
Transient directing ligands for selective metal-catalysed C-H activation.
Nat Rev Chem. 2021 Sep;5(9):646-659. doi: 10.1038/s41570-021-00311-3. Epub 2021 Jul 20.
2
Chiral CpRh complexes for C-H functionalization reactions.
Sci Bull (Beijing). 2021 Feb 15;66(3):210-213. doi: 10.1016/j.scib.2020.09.035. Epub 2020 Sep 29.
3
Ligand-ligated Ni-Al bimetallic catalysis for C-H and C-C bond activation.
Chem Commun (Camb). 2022 Nov 3;58(88):12260-12273. doi: 10.1039/d2cc04274f.
4
Enantioselective C2-H Alkylation of Pyridines with 1,3-Dienes via Ni-Al Bimetallic Catalysis.
J Am Chem Soc. 2022 Oct 19;144(41):18810-18816. doi: 10.1021/jacs.2c09306. Epub 2022 Oct 7.
5
Enantioselective Nickel-Catalyzed C(sp )-H Activation of Formamides.
Angew Chem Int Ed Engl. 2022 Oct 17;61(42):e202209625. doi: 10.1002/anie.202209625. Epub 2022 Sep 12.
6
Ni-catalyzed hydroarylation of alkynes with unactivated β-C(sp)-H bonds.
Nat Commun. 2022 May 26;13(1):2938. doi: 10.1038/s41467-022-30367-8.
7
Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds.
Angew Chem Int Ed Engl. 2022 Feb 21;61(9):e202113343. doi: 10.1002/anie.202113343. Epub 2021 Dec 21.
9
C-H Activation: Toward Sustainability and Applications.
ACS Cent Sci. 2021 Feb 24;7(2):245-261. doi: 10.1021/acscentsci.0c01413. Epub 2021 Feb 2.
10

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