Photocatalyzed Direct C(sp)-H Alkenylation of Unactivated Alkanes via Tandem C-C Activation of Cyclopropenes.

A highly adaptable method has been developed for the alkenylation of a broad spectrum of inert alkanes, employing milder reaction conditions. Tetrabutylammonium decatungstate (TBADT) serves as a photocatalyst for hydrogen atom transfer (HAT), instigating the formation of transient alkyl radicals through C(sp)-H functionalization. These radicals exhibit regioselective addition to cyclopropenes, followed by the subsequent activation of C-C bonds, forming the corresponding vinylated derivatives. This methodology accommodates diverse unreactive C(sp)-H bond motifs and multisubstituted cyclopropenes, enabling the efficient synthesis of highly functionalized olefins with high diastereoselectivity.