Iron-Catalyzed Vinylic C-H Alkylation with Alkyl Peroxides

Chemistry, an Asian Journal
Liang GeHongli Bao

Abstract

A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C-H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.

References

Jun 6, 2002·Journal of the American Chemical Society·Yousuke IkedaKoichiro Oshima
Jul 22, 2006·Angewandte Chemie·Shu-Li You, Li-Xin Dai
Aug 28, 2007·Journal of the American Chemical Society·Luke Firmansjah, Gregory C Fu
Feb 14, 2008·Journal of the American Chemical Society·Yuhua ZhangChao-Jun Li
Mar 22, 2008·Angewandte Chemie·Lukas J GoossenKäthe Goossen
Apr 15, 2009·Journal of the American Chemical Society·Daisuke NodaHideo Nagashima
Nov 20, 2009·Organic Letters·Rushi Trivedi, Jon A Tunge
Jun 22, 2010·Beilstein Journal of Organic Chemistry·Lukas J GooßenThomas Knauber
Oct 5, 2010·Organic Letters·Zhengjiang FuMaochun Hong
Jan 18, 2011·Chemical Reviews·Jimmie D WeaverJon A Tunge
Jul 28, 2011·Chemical Society Reviews·Nuria Rodríguez, Lukas J Goossen
Nov 22, 2011·Journal of the American Chemical Society·Kayla S BloomeErik J Alexanian
Feb 10, 2012·Journal of the American Chemical Society·Zhentao WangChaozhong Li
Feb 11, 2012·Journal of the American Chemical Society·Montserrat Rueda-BecerrilGlenn M Sammis
Jun 15, 2012·Journal of the American Chemical Society·Feng YinChaozhong Li
Aug 23, 2012·Journal of the American Chemical Society·Xuesong LiuChaozhong Li
Aug 29, 2012·Angewandte Chemie·Martin J Schnermann, Larry E Overman
Jan 21, 2014·Journal of the American Chemical Society·Montserrat Rueda-BecerrilJean-François Paquin
Mar 1, 2014·Chemical Communications : Chem Comm·Yinjun Zou, Jianrong Steve Zhou
Mar 29, 2014·Angewandte Chemie·Daniel A DiroccoMatthew Tudge
Apr 24, 2014·Angewandte Chemie·Caitlin M McMahon, Erik J Alexanian
Sep 18, 2014·Journal of the American Chemical Society·Simon B LangJon A Tunge
Oct 14, 2014·Chemical Society Reviews·Chao ShenXiaogang Liu
Feb 5, 2015·Chemical Communications : Chem Comm·Changduo PanChengjian Zhu
Apr 18, 2015·Journal of the American Chemical Society·Sandrine VentreDavid W C MacMillan
Jul 29, 2015·Journal of the American Chemical Society·Chao LiuChaozhong Li
Feb 3, 2016·Journal of the American Chemical Society·Josep CornellaPhil S Baran
Feb 20, 2016·The Journal of Organic Chemistry·Asik HossianRanjan Jana

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Citations

Feb 24, 2021·Organic & Biomolecular Chemistry·Shintaro KawamuraMikiko Sodeoka
Dec 20, 2019·Organic Letters·Xiaotao ZhuHongli Bao
Jan 23, 2019·Organic Letters·Haigen XiongHongli Bao

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