Iron-Catalyzed Decarboxylative Olefination of Cycloketone Oxime Esters with α,β-Unsaturated Carboxylic Acids via C-C Bond Cleavage

Organic Letters
Jing-Feng ZhaoLi Na Guo

Abstract

An iron-catalyzed redox-neutral, decarboxylative olefination of cycloketone oxime esters with α,β-unsaturated carboxylic acids has been developed. This reaction involves an iminyl radical mediated C-C bond cleavage/radical addition/decarboxylation cascade. This protocol is highlighted by its low-cost catalytic system and readily accessible starting materials, as well as broad substrate scope, thus providing facile access to structurally diverse cyano-containing alkenes.

References

Aug 4, 2004·The Journal of Organic Chemistry·Takahiro NishimuraSakae Uemura
Dec 9, 2004·Chemical Reviews·Carsten BolmLorenzo Zani
Nov 13, 2007·Nature·Amir H Hoveyda, Adil R Zhugralin
May 24, 2008·Chemical Society Reviews·Arkaitz CorreaCarsten Bolm
Jul 1, 2008·Accounts of Chemical Research·Benjamin D Sherry, Alois Fürstner
May 9, 2009·ChemSusChem·Waldemar Maximilian CzaplikAxel Jacobi von Wangelin
Sep 2, 2010·Journal of Medicinal Chemistry·Fraser F FlemingBrian C Shook
Nov 6, 2010·Chemical Reviews·Chang-Liang SunZhang-Jie Shi
Jul 28, 2011·Chemical Society Reviews·Nuria Rodríguez, Lukas J Goossen
Jul 5, 2012·Chemical Communications : Chem Comm·Hailong YangJincheng Mao
Jan 3, 2015·Chemical Society Reviews·Shan TangAiwen Lei
Jul 5, 2016·Organic & Biomolecular Chemistry·Li-Na GuoXin-Hua Duan
Dec 21, 2016·Chemistry : a European Journal·Hai-Bin Yang, Nicklas Selander
Mar 8, 2017·Chemical Reviews·Ye WeiWeiping Su
May 6, 2017·Nature Communications·Jiefeng HuZhuangzhi Shi
Sep 1, 2017·Journal of the American Chemical Society·Bo QianHongli Bao
Dec 6, 2017·Chemistry : a European Journal·Mary M JackmanSteven L Castle

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Citations

Mar 23, 2019·Chemical Society Reviews·Paramasivam SivaguruXihe Bi
Apr 2, 2019·Chemical Communications : Chem Comm·Zhiping YinXiao-Feng Wu

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