Synthesis of Trifluoromethyl-Substituted Cyclopentanes through Boron-Radical-Catalyzed Cycloaddition Reaction of Trifluoromethyl-Substituted Alkenes

Lulu Qin; Tao Yu; Zhengwei Ding; Min Zhao; Pengfei Li

doi:10.1055/a-2511-4274

Synthesis, Inhaltsverzeichnis

Synthesis
DOI: 10.1055/a-2511-4274

paper

Boryl Radical Chemistry

Synthesis of Trifluoromethyl-Substituted Cyclopentanes through Boron-Radical-Catalyzed Cycloaddition Reaction of Trifluoromethyl-Substituted Alkenes

Lulu Qin

^aFrontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China

,

Tao Yu

^aFrontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China

,

Zhengwei Ding

^bDepartment of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, P. R. of China

,

Min Zhao

^aFrontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China

,

Pengfei Li ∗

^aFrontier Institute of Science and Technology, Xi’an Jiaotong University, Xi’an 710054, P. R. of China

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

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Abstract

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Abstract

A highly efficient protocol for the synthesis of trifluoromethyl-substituted cyclopentanes, a structural motif ubiquitous in bioactive compounds and natural products, via boron-radical-catalyzed (3+2) cycloaddition of aroylcyclopropanes and trifluoromethyl-substituted alkenes was developed. Employing readily available precursors, this modular, atom-economical, metal-free, and operationally simple process was compatible with diverse functional groups, giving the products in generally good to high yields. Trifluoromethyl-substituted bicyclo[2.1.1]hexanes (BCHs) were analogously prepared.

Key words

cycloaddition - trifluoromethyl-substituted alkenes - boron radicals - catalysis - cyclopentanes

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