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

Org Lett. 2021 Nov 5;23(21):8622-8627. doi: 10.1021/acs.orglett.1c03336. Epub 2021 Oct 18.

Authors

Gi Uk Han¹, Seohyun Shin¹, Yonghyeon Baek¹, Dongwook Kim^{2

3}, Kooyeon Lee⁴, Jeung Gon Kim⁵, Phil Ho Lee¹

Affiliations

¹ Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea.
² Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.
³ Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Republic of Korea.
⁴ Department of Bio-Health Technology, Kangwon National University, Chuncheon 24341, Republic of Korea.
⁵ Department of Chemistry, Research Institute of Physics and Chemistry, Jeonbuk National University, Jeonju 54896, Republic of Korea.

PMID: 34662139
DOI: 10.1021/acs.orglett.1c03336

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.