Abstract Cyclobutanols are privileged cyclic skeletons in natural products and synthetic building blocks. C(sp3)−H functionalization is a prolonged challenge in organic synthesis. The synthesis of cyclobutanols through double C(sp3)-H bond functionalization remains elusive. Here we report the efficient synthesis of cyclobutanols through intermolecular radical 3 + 1 cascade cyclization, involving the functionalization of two C − H bonds through sequential hydrogen atom transfer. The copper complex reduces the iodomethylsilyl alcohols efficiently under blue-light irradiation to initiate the tandem transformation. The mild reaction tolerates a broad range of functional groups and allows for the facile generation of elaborate polycyclic structures.