Site- and enantioselective B−H functionalization of carboranes

Functionalization of carboranes, icosahedral boron-carbon molecular clusters, is of great interest as they have wide applications in medicinal and materials chemistry. Thus, site- and enantioselective synthesis of carboranes requires complete control of the reaction. Herein, we describe the asymmetric Rh(II)-catalyzed insertion reactions of carbenes into cage B-H bond of carboranes. This reaction thereby generates carboranes possessing a carbon-stereocenter adjacent to cage boron of the carborane, in excellent site- and enantioselectivity under mild reaction conditions. The fully computed transition structures of Rh(II)-catalyzed carbene insertion process through density functional theory are reported. These B-H insertion transition structures, in conjunction with topographical proximity surfaces analyses, visually reveal the region between the carborane and the phthalimide ligands responsible for the selectivities of this reaction.

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Publication Details

Journal
Nature Communications
Published
2025-05-05
DOI
https://doi.org/10.1038/s41467-025-59410-0
Citations
11
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
14.96

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article

Site- and enantioselective B−H functionalization of carboranes

Abdikani Omar Farah, Hyeonsik Eom, Phil Ho Lee, Henry R. Wise et al.
11 citations
Nature Communications
Boron Compounds in Chemistry
14.96
article

Site- and enantioselective B−H functionalization of carboranes

Abdikani Omar Farah, Hyeonsik Eom, Phil Ho Lee, Henry R. Wise, Kyungsup Lee, Hee Chan Noh, Gisela A. González‐Montiel, Paul Ha‐Yeon Cheong, Dongwook Kim, Tae Hyeon Kim
article en
11 citations

Abstract

Functionalization of carboranes, icosahedral boron-carbon molecular clusters, is of great interest as they have wide applications in medicinal and materials chemistry. Thus, site- and enantioselective synthesis of carboranes requires complete control of the reaction. Herein, we describe the asymmetric Rh(II)-catalyzed insertion reactions of carbenes into cage B-H bond of carboranes. This reaction thereby generates carboranes possessing a carbon-stereocenter adjacent to cage boron of the carborane, in excellent site- and enantioselectivity under mild reaction conditions. The fully computed transition structures of Rh(II)-catalyzed carbene insertion process through density functional theory are reported. These B-H insertion transition structures, in conjunction with topographical proximity surfaces analyses, visually reveal the region between the carborane and the phthalimide ligands responsible for the selectivities of this reaction.

Nature CommunicationsVol. 16(1)
Oregon State University (US), Korea Advanced Institute of Science and Technology (KR), Kangwon National University (KR), Institute for Basic Science (KR)
National Science Foundation, National Research Foundation, National Research Foundation of Korea, Korea Advanced Institute of Science and Technology, Division of Chemistry
Openalex Percentile: Top 1%
Boron Compounds in Chemistry
14.96
DOIOpen Access PDFOpenAlex
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