Iridium(III)-Catalyzed Regioselective B(4)-H Amination of o-Carboranes with Sufilimines

Iridium(III)-catalyzed regioselective B(4)-H aminationisdeveloped from the reaction of o-carborane acidswith sulfilimines without any oxidants under mild conditions, whichleads to a wide range of B(4)-H aminated o-carboranes in good yields with a broad substrate scope. Moreover,the selective B(3,6)-diamination reaction of the o-carborane acid was achieved. The present reaction is attractivefrom a practical point of view because dibenzothiophene is quantitativelyrecovered and reused.

Automated summary

A regioselective B(4)-H amination reaction was developed using Iridium(III) catalyst from the reaction of o-carborane acids with sulfilimines, without the need for oxidants under mild conditions. This reaction resulted in a wide range of B(4)-H aminated o-carboranes in good yields and with a broad substrate scope. Additionally, selective B(3,6)-diamination of the o-carborane acid was achieved. One practical advantage of this reaction is the quantitative recovery and reuse of dibenzothiophene.