Recyclable Aliphatic Nitrile-Template Enabled Remote -C-H Functionalization at Room Temperature.

This article describes the development of a new aliphatic nitrile-template-directed remote -selective C-H olefin functionalization reaction of arenes. Remarkably, unlike the previous reports, this process is feasible at room temperature and enabled the formation of products with excellent regioselectivity. The present protocol encompasses a broad spectrum of substituted dihydrocinnamic acids and olefins, producing -C-H olefinated products (up to 96% yield). In addition, the efficacy of the present method has been showcased by the synthesis of various drug analogues (e.g., cholesterol, estrone, ibuprofen, and naproxen). Significantly, the robustness of -olefination was also demonstrated by gram-scale synthesis. The new nitrile-based -directing template, in particular, could be easily synthesized in two steps and recycled under mild conditions.