Iron-Catalyzed Deboronation/Cyanoalkylation of Vinyl Boronic Acids with Cyclobutanone Ketoximes

Hua-Wei Zhang; Yu-Zhao Wang; Xiu-Fen Cheng; Han-Yue Zhang; Zi-Ying Wang; Nuo Xu; Yan-Qi Su; Yan Li

doi:10.1055/s-0040-1720140

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(23): 3653-3659
DOI: 10.1055/s-0040-1720140

paper

Iron-Catalyzed Deboronation/Cyanoalkylation of Vinyl Boronic Acids with Cyclobutanone Ketoximes

Hua-Wei Zhang‡

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Yu-Zhao Wang‡

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Xiu-Fen Cheng

^bCollege of Chemistry, Chemical Engineering and Materials Science, Institute of Biomedical Sciences, Shandong Normal University, Jinan 250014, P. R. of China

,

Han-Yue Zhang

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Zi-Ying Wang

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Nuo Xu

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Yan-Qi Su

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

,

Yan Li∗

^aSchool of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China

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Abstract

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Abstract

In this paper, an iron-catalyzed deboronation/cyanoalkylation of vinyl boronic acids for the preparation of distal cyanoalkyl alkenes with vinyl boronic acids as radical acceptor and activator is reported. In this reaction, various cyclobutanone oximes and substituted vinyl boronic acids can be transformed into the corresponding cyanoalkylated alkenes in moderate to good yields under these conditions. Mechanistic studies indicated that a single-electron transfer process may be involved in this transformation.

Key word

iron catalysis - cyclobutanone oximes - N–O bond cleavage - iminyl radical - cyanoalkylation

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Referenzen

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