Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones

Gi Uk Han; Seohyun Shin; Yonghyeon Baek; Dongwook Kim; Kooyeon Lee; Jeung Gon Kim; Phil Ho Lee

doi:10.1021/acs.orglett.1c03336

Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones

Gi Uk Han
, Seohyun Shin
, Yonghyeon Baek
, Dongwook Kim
, Kooyeon Lee
, Jeung Gon Kim^*
, Phil Ho Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

34 Scopus citations

Abstract

Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds smoothly without organic solvents or external heating, the present method is regarded as a sustainable and environmentally friendly surrogate for typical solvent-based reactions.

Original language	English
Pages (from-to)	8622-8627
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.1c03336
State	Published - 2021.11.5

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Chemistry
Biological Sciences

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10.1021/acs.orglett.1c03336

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@article{c9c0529cf33042e1be44da176d7bce6c,

title = "Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones",

abstract = "Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds smoothly without organic solvents or external heating, the present method is regarded as a sustainable and environmentally friendly surrogate for typical solvent-based reactions.",

author = "Han, \{Gi Uk\} and Seohyun Shin and Yonghyeon Baek and Dongwook Kim and Kooyeon Lee and Kim, \{Jeung Gon\} and Lee, \{Phil Ho\}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = nov,

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doi = "10.1021/acs.orglett.1c03336",

language = "English",

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journal = "Organic Letters",

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T1 - Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones

AU - Han, Gi Uk

AU - Shin, Seohyun

AU - Baek, Yonghyeon

AU - Kim, Dongwook

AU - Lee, Kooyeon

AU - Kim, Jeung Gon

AU - Lee, Phil Ho

PY - 2021/11/5

Y1 - 2021/11/5

N2 - Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds smoothly without organic solvents or external heating, the present method is regarded as a sustainable and environmentally friendly surrogate for typical solvent-based reactions.

AB - Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds smoothly without organic solvents or external heating, the present method is regarded as a sustainable and environmentally friendly surrogate for typical solvent-based reactions.

UR - https://www.scopus.com/pages/publications/85118719091

U2 - 10.1021/acs.orglett.1c03336

DO - 10.1021/acs.orglett.1c03336

M3 - Journal article

C2 - 34662139

AN - SCOPUS:85118719091

SN - 1523-7060

VL - 23

SP - 8622

EP - 8627

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones

Abstract

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