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Cycloalkylation of C(sp3)‑H Bond with Neighboring Carboxylic Acid as Traceless Activating Group

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journal contribution
posted on 17.02.2017, 00:00 by Leiyang Lv, Zhiping Li
Selective functionalization of inert C­(sp3)-H bond is one of cutting-edge challenges in chemical synthesis. A novel strategy for selective C­(sp3)-H bond cycloalkylation is developed with neighboring carboxylic acid as a traceless activating group. Primary and secondary alkyl carboxylic acids undergo decarboxylation/α-C­(sp3)-H cleavage/cycloalkylation to give the five-membered cyclization products, while tertiary acids undergo decarboxylation/β-C­(sp3)-H cleavage/cycloalkylation to generate the six-membered cyclization products.