Iridium(III)-Catalyzed B(4)-Acylmethylation and B(3,5)-Diacylmethylation from o-Carboranes and Sulfoxonium Ylides

Gi Hoon Ko; Kyusik Um; Hee Chan Noh; Jin Young Kim; Haneal Jeong; Chanyoung Maeng; Sang Hoon Han; Gi Uk Han; Phil Ho Lee

doi:10.1021/acs.orglett.2c00103

Iridium(III)-Catalyzed B(4)-Acylmethylation and B(3,5)-Diacylmethylation from o-Carboranes and Sulfoxonium Ylides

Org Lett. 2022 Mar 4;24(8):1604-1609. doi: 10.1021/acs.orglett.2c00103. Epub 2022 Feb 17.

Authors

Gi Hoon Ko¹, Kyusik Um^{1

2}, Hee Chan Noh¹, Jin Young Kim¹, Haneal Jeong¹, Chanyoung Maeng¹, Sang Hoon Han¹, Gi Uk Han¹, Phil Ho Lee^{1

2}

Affiliations

¹ Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea.
² KIIT (Kangwon Institute of Inclusive Technology), Kangwon National University, Chuncheon 24341, Republic of Korea.

PMID: 35175779
DOI: 10.1021/acs.orglett.2c00103

Abstract

An iridium(III)-catalyzed regioselective acylmethylation of the cage B(4)-H bond in o-carborane acids with sulfoxonium ylides is demonstrated through B(4)-H activation in ethanol under very mild conditions, affording a number of B(4)-acylmethylated o-carboranes. Additionally, the selective sequential B(4)- and B(6)-acylmethylation reactions finally gave B(3,5)-diacylmethylated o-carboranes in one pot.