Photoinduced α-C(sp3)–H functionalization of cyclic ethers via synergistic photocatalysis and HAT for efficient C–C bond formation

Abstract

The selective transformation of inert C(sp³)–H bonds remains a significant challenge in modern organic synthesis. Herein, we report a photocatalytic strategy for achieving the efficient and selective C–H bond activation under mild conditions. Using di-tert-butyl peroxide (DTBP) as a dual-functional reagent, this protocol enables the generation of sp³ carbon radical species of cyclic ethers, followed by radical addition to simple alkenes, including styrene, 4-phenyl-1-butene, and phenoxyallyl derivatives. Through the synergistic effect of photoexcitation and hydrogen atom transfer (HAT), this strategy facilitates the construction of C–C bonds between cyclic ethers and unactivated alkenes, to yield highly functionalized ether skeletons. This approach aligns with the principles of green chemistry and extends the scope of photocatalysis in complex molecular synthesis, providing valuable insights for related photocatalytic oxidative coupling reactions.