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Selective functionalization of inert C(sp 3 )-H bond is one of cutting-edge challenges in chemical synthesis. A novel strategy for selective C(sp 3 )-H bond cycloalkylation is developed with neighboring carboxylic acid as a traceless activating group. Primary and secondary alkyl carboxylic acids undergo decarboxylation/α-C(sp 3 )-H cleavage/cycloalkylation to give the five-membered cyclization products, while tertiary acids undergo decarboxylation/β-C(sp 3 )-H cleavage/cycloalkylation to generate the six-membered cyclization products.
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Lv et al. (2017) studied this question.
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