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评估一种碘代异恶唑鎓(III)盐的卤键强度。

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt.

作者信息

Reinhard Dominik L, Schmidt Anna, Sons Marc, Wolf Julian, Engelage Elric, Huber Stefan M

机构信息

Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany.

出版信息

Beilstein J Org Chem. 2024 Sep 23;20:2401-2407. doi: 10.3762/bjoc.20.204. eCollection 2024.

Abstract

Diaryliodonium(III) salts have been established as powerful halogen-bond donors in recent years. Herein, a new structural motif for this compound class was developed: iodoloisoxazolium salts, bearing a cyclic five-membered iodolium core fused with an isoxazole ring. A derivative of this class was synthesized and investigated in the solid state by X-ray crystallography. Finally, the potential as halogen-bonding activator was benchmarked in solution in the gold-catalyzed cyclization of a propargyl amide.

摘要

近年来,二芳基碘鎓(III)盐已被确立为强大的卤素键供体。在此,开发了这类化合物的一种新结构 motif:碘代异恶唑鎓盐,其具有与异恶唑环稠合的环状五元碘鎓核心。合成了该类的一种衍生物,并通过X射线晶体学对其固态进行了研究。最后,在炔丙基酰胺的金催化环化反应中,在溶液中对其作为卤素键活化剂的潜力进行了基准测试。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9d18/11443664/122e98f8b989/Beilstein_J_Org_Chem-20-2401-g002.jpg

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本文引用的文献

1
N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.
Chemistry. 2021 Sep 15;27(52):13128-13134. doi: 10.1002/chem.202101961. Epub 2021 Aug 5.
2
Iodine(III)-Based Halogen Bond Donors: Properties and Applications.
Chem Rec. 2021 Aug;21(8):1912-1927. doi: 10.1002/tcr.202100119. Epub 2021 Jun 18.
3
A Bidentate Iodine(III)-Based Halogen-Bond Donor as a Powerful Organocatalyst*.
Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5069-5073. doi: 10.1002/anie.202013172. Epub 2021 Jan 15.
4
Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications.
Org Lett. 2020 Sep 18;22(18):7261-7266. doi: 10.1021/acs.orglett.0c02593. Epub 2020 Sep 3.
5
Activation of a Metal-Halogen Bond by Halogen Bonding.
Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16496-16500. doi: 10.1002/anie.202005214. Epub 2020 Jul 10.
6
Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases.
J Am Chem Soc. 2020 Mar 18;142(11):5221-5233. doi: 10.1021/jacs.9b12998. Epub 2020 Mar 3.
7
Iodine(III) Derivatives as Halogen Bonding Organocatalysts.
Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3830-3833. doi: 10.1002/anie.201713012. Epub 2018 Mar 2.
8
Halogen bonding anion recognition.
Chem Commun (Camb). 2016 Jul 5;52(56):8645-58. doi: 10.1039/c6cc03638d.
9
The Halogen Bond.
Chem Rev. 2016 Feb 24;116(4):2478-601. doi: 10.1021/acs.chemrev.5b00484. Epub 2016 Jan 26.
10
Arylation with Diaryliodonium Salts.
Top Curr Chem. 2015 Oct 27. doi: 10.1007/128_2015_661.

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