A One Carbon Linchpin for Rh(III)-Catalyzed, C(sp3)-Directed C–H Annulation

We disclose a new platform for C(sp3)-directed C–H annulations to generate valuable heterocycles from readily available starting materials. A commercially available one carbon linchpin is leveraged to access alkyl boron species from simple anilines. Rhodium-catalyzed C(sp3) transmetallation from this key intermediate provides a C–Rh bond appropriately positioned for ortho-C–H activation, enabling formation of C,C-rhodacycles. With the addition of a variety of alkyne coupling partners, diverse dihydroquinolines are synthesized.