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Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp³)-H amidation, C(sp²)-H iodination, and perfluoroalkylation reactions.

ABSTRACT: A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp³ C-H amidation reactions of alkyl ethers and benzylic hydrocarbons, C-H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and tBuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.

SUBMITTER: Wang Y

PROVIDER: S-EPMC9930934 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp3)-H amidation, C(sp2)-H iodination, and perfluoroalkylation reactions.

Wang Yaxin Y Cao Zehui Z He Qin Q Huang Xin X Liu Jiaxi J Neumann Helfried H Chen Gong G Beller Matthias M

Chemical science 20230124 7

A simple, efficient, and convenient activation of perfluoroalkyl iodides by tBuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp3 C-H amidation reactions of alkyl ethers and benzylic hydrocarbons, C-H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and t ...[more]

PMID: 36819859

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