Gold(I)-Catalyzed and H2 O-Mediated Carbene Cascade Reaction of Propargyl Diazoacetates: Furan Synthesis and Mechanistic Insights

Organic Letters
Ming BaoXinfang Xu

Abstract

A novel gold-catalyzed water-mediated carbene cascade reaction of propargyl diazoacetates has been developed. Mechanistic investigation indicates that this reaction is initiated by gold-catalyzed gold-carbene formation followed by an unprecedented 6- endo-dig carbocyclization with tethered alkyne through an oxonium ylide intermediate, terminated by a β-H elimination/protodeauration process to give the aromatized furan products in good to high yields with broad substrate generality. Notably, the proposed gold-carbene intermediates are verified by interception experiments.

References

Jul 18, 2001·Journal of the American Chemical Society·G A Moniz, J L Wood
Jan 18, 2003·The Journal of Organic Chemistry·Albert Padwa, Christopher S Straub
Aug 2, 2003·Journal of the American Chemical Society·H V Rasika DiasCarl J Lovely
Dec 22, 2005·Journal of the American Chemical Society·Magnus J JohanssonF Dean Toste
Apr 17, 2007·Journal of the American Chemical Society·Cole A WithamF Dean Toste
Apr 20, 2007·Journal of the American Chemical Society·Janelle L Thompson, Huw M L Davies
Jun 20, 2007·Chemical Society Reviews·Huw M L Davies, Simon J Hedley
Jun 22, 2007·Chemical Reviews·A Stephen K Hashmi
Jun 26, 2008·Journal of the American Chemical Society·Nathan D Shapiro, F Dean Toste
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Jun 8, 2011·Beilstein Journal of Organic Chemistry·Lei ZhouJianbo Wang
Jun 2, 2012·Accounts of Chemical Research·Shou-Fei Zhu, Qi-Lin Zhou
Aug 16, 2012·Chemical Communications : Chem Comm·Xia ZhaoJianbo Wang
May 25, 2013·Journal of the American Chemical Society·Renhe LiuWeiping Tang
Aug 28, 2013·Journal of the American Chemical Society·John F Briones, Huw M L Davies
Sep 21, 2013·Journal of the American Chemical Society·Pascal NöselA Stephen K Hashmi
Nov 20, 2013·Accounts of Chemical Research·Xin Guo, Wenhao Hu
Jan 17, 2014·Accounts of Chemical Research·Liming Zhang
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Dec 15, 2015·Chemical Society Reviews·Lu Liu, Junliang Zhang
May 4, 2016·Chemical Communications : Chem Comm·Manuel R FructosPedro J Pérez
Jul 23, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Veronica D'AngeloMarcello Locatelli

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