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.

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