A Neutral FeCl3 Photocatalysis for C–C Bond Animation and Alkylation of Cyclic Alcohols

Zongnan Zhang; Ting Xue; Zhe Han; Rong Zeng

doi:10.1055/a-1966-3271

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(03): 433-442
DOI: 10.1055/a-1966-3271

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A Neutral FeCl₃ Photocatalysis for C–C Bond Animation and Alkylation of Cyclic Alcohols

Zongnan Zhang‡

^aSchool of Chemistry, Xi’an Jiaotong University, Xi’an 710049, P. R. of China

,

Ting Xue‡

^aSchool of Chemistry, Xi’an Jiaotong University, Xi’an 710049, P. R. of China

,

Zhe Han

^bSchool of Nuclear Science and Technology, Xi’an Jiaotong University, Xi’an 710049, P. R. of China

,

Rong Zeng ∗

^aSchool of Chemistry, Xi’an Jiaotong University, Xi’an 710049, P. R. of China

^cGuangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, Guangdong, P. R. of China

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Abstract

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Abstract

A modified method for iron-catalyzed C–C bond cleavage and amination and alkylation of nonactivated cyclic alcohols has been developed. Using FeCl₃ as catalyst, the photoinduced ligand-to-metal charge transfer facilitates the generation of O-radicals from alcohols, the subsequent β-scission, and finally the radical trapping. Compared with the Fe(OR)₃ catalysis, this mildly base-free system could enable the amination in a broader substrate scope with higher yields. Moreover, the C–C bond cleavage and alkylation of cyclic alcohols proceeds with electron-deficient olefins under these conditions.

Key words

iron catalysis - photocatalysis - C–C bond cleavage - amination - alkylation

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