Site- and enantioselective B−H functionalization of carboranes

Kyungsup Lee, Gisela A. González-Montiel, Hyeonsik Eom, Tae Hyeon Kim, Hee Chan Noh, Abdikani Omar Farah, Henry R. Wise, Dongwook Kim, Paul Ha-Yeon Cheong () and Phil Ho Lee ()
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Kyungsup Lee: Kangwon National University
Gisela A. González-Montiel: 153 Gilbert Hall
Hyeonsik Eom: Kangwon National University
Tae Hyeon Kim: Kangwon National University
Hee Chan Noh: Kangwon National University
Abdikani Omar Farah: 153 Gilbert Hall
Henry R. Wise: 153 Gilbert Hall
Dongwook Kim: Korea Advanced Institute of Science and Technology
Paul Ha-Yeon Cheong: 153 Gilbert Hall
Phil Ho Lee: Kangwon National University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: 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.

Date: 2025
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DOI: 10.1038/s41467-025-59410-0

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