Transition-Metal-Free C(sp3)-H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer.

Here we report a unique transition-metal-free C(sp3)-H/C(sp3)-H coupling of cycloalkanes at room temperature. Unactivated cycloalkanes and 2-azaallyls underwent the combination process of single-electron transfer (SET) and hydrogen atom transfer (HAT) to deliver a wide variety of cycloalkane-functionalized products. This expedient approach enables C(sp3)-H/C(sp3)-H coupling of cycloalkanes under mild conditions without transition metals, initiators, and oxidants.