Iridium(III)-Catalyzed Asymmetric Site-Selective Carbene C-HInsertion during Late-Stage Transformation

C-H functionalization has recently received con-siderable attention because C-H functionalization during the late-stage transformation is a strong and useful tool for the modificationof the bioactive compounds and the creation of new activemolecules. Although a carbene transfer reaction can directlyconvert a C-H bond to the desired C-C bond in a stereoselectivemanner, its application in late-stage material transformation islimited. Here, we observed that the iridium-salen complex6exhibited efficient catalysis in asymmetric carbene C-H insertionreactions. Under optimized conditions, benzylic, allylic, andpropargylic C-H bonds were converted to desired C-C bondsin an excellent stereoselective manner. Excellent regioselectivitywas demonstrated in the reaction using not only simple substrate but also natural products, bearing multiple reaction sites.Moreover, based on the mechanistic studies, the iridium-catalyzed unique C-H insertion reaction involved rate-determiningasynchronous concerted processes

Automated summary

C-H functionalization is a powerful tool for modifying bioactive compounds and creating new active molecules in late-stage transformations. However, its application is limited. This study demonstrates the efficient catalysis of an iridium-salen complex in asymmetric carbene C-H insertion reactions, achieving high stereoselectivity and regioselectivity.