Transition-metal-catalyzed direct and regioselective C–H bond activation/functionalization is a highly efficient and straightforward tool that is useful in the field of organic synthesis and total synthesis. Driven by the need for a more efficient synthetic route to the kinase inhibitors, we have explored one-pot catalysis of tandem processes for generating molecular complexity from simple starting materials by employing a single catalyst in a single reaction vessel. Cyclopropane is also widely used as a conformational restricting framework in medicinal chemistry, and arylated cyclopropanes are a privileged class of structures found in many biologically active molecules. In this regards, transition-metal-catalyzed asymmetric C–H arylation of cyclopropanes has been the focus of great research interest. We hypothesized that an appropriate chiral bidentate directing group embedded in the substrate could induce high levels of stereocontrol during C–H functionalization via a steric repulsion. With efficient synthetic routes in hand, we have studied application of the structure-based design to identify potent kinase inhibitors and ultimately streamline late-stage drug modification. Ongoing results in this direction and future plan will be presented and discussed