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Ortho-Carborane-Derived Halogen Bonding Organocatalysts

17 December 2024, Version 2
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Multidentate neutral halogen bonding (XB) catalysts based on iodinated icosahedral ortho-carborane moieties are introduced. Co-crystallization-studies, calorimetric measurements, and 1H NMR titrations demonstrate their strong binding to halides and neutral compounds, further underlined by quantum-chemical calculations. Thus, their superior Lewis acidity compared to traditional perfluorinated halogen-bond donors has been shown. The iodocarborane catalysts also outperformed the latter in a halide abstraction reaction and catalyzed a nitro-Michael addition reaction, which was previously out of reach for neutral XB-based organocatalysts.

Keywords

halogen bonding
noncovalent interactions
ortho-carboranes
calorimetry

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Synthesis of halogen bond donors, spectroscopic data, calorimetry data, crystallographic data, computational data.
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Version History

Dec 17, 2024 Version 2

Version Notes

An erroneous statement was corrected: the inactive dicationic halogen bonding catalyst that was inactive in the reaction of Scheme was not catalyst 6 (which was not tested in this reaction), but was based on iodotriazolium motifs. This still illustrates the challenging nature of this reaction. We apologize for the confusion.

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-19c30-v2
D O I: 10.26434/chemrxiv-2024-19c30-v2 [opens in a new tab]

Funding

Deutsche Forschungsgemeinschaft
EXC 2033 - 390677874

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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