Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes

Journal of the American Chemical Society
Robert T Yu, Tomislav Rovis

Abstract

A rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition between alkenyl isocyanates and alkynes has been developed. Heating a mixture of an alkenyl isocyanate and a symmetrical internal alkyne in the presence of [Rh(ethylene)2Cl]2/P(4-OMe-C6H4)3 in toluene delivers substituted indolizinones and quinolizinones. Depending on the substrates, a rare fragmentation of the isocyanate unit can be involved within the cycloaddition process to furnish a vinylogous amide embedded in the indolizinone.

References

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Citations

Jul 29, 2010·Journal of the American Chemical Society·Todd K Hyster, Tomislav Rovis
Sep 16, 2010·Journal of the American Chemical Society·Tomoya MiuraMasahiro Murakami
Mar 16, 2011·Journal of the American Chemical Society·Kevin M Oberg, Tomislav Rovis
Jun 6, 2012·Journal of the American Chemical Society·Zhi HeAndrei K Yudin
Feb 28, 2008·Journal of the American Chemical Society·Robert T Yu, Tomislav Rovis
Jul 3, 2009·Journal of the American Chemical Society·Rebecca Keller Friedman, Tomislav Rovis
Oct 12, 2010·The Journal of Organic Chemistry·Micah J NiphakisGunda I Georg
Dec 7, 2011·The Journal of Organic Chemistry·Gen OnoderaRyo Takeuchi
Sep 11, 2009·Organic Letters·Brendan R D'Souza, Janis Louie
Oct 3, 2008·Chemical Communications : Chem Comm·Andrew McIverAlexander Deiters
Sep 28, 2010·Chemical Communications : Chem Comm·Takuya OzawaSeijiro Matsubara
Mar 8, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Chung-Yeh WuYi-Hung Liu
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Emily M HarcourtDarren G Hamilton
Jul 14, 2010·Pure and Applied Chemistry. Chimie Pure Et Appliquée·Rebecca Keller FriedmanTomislav Rovis
Jan 31, 2014·Organic Letters·Kaila A MargreyJonathan R Scheerer
Oct 23, 2015·Chemical Communications : Chem Comm·Amit Kumar Chattopadhyay, Stephen Hanessian
May 21, 2016·Organic & Biomolecular Chemistry·James D Neuhaus, Michael C Willis
May 26, 2007·Angewandte Chemie·Douglas D Young, Alexander Deiters
Oct 23, 2009·Chemical Society Reviews·Stéphane Perreault, Tomislav Rovis
Jan 5, 2008·Organic & Biomolecular Chemistry·Lakshminath SripadaAlexander Deiters
Sep 26, 2019·Angewandte Chemie·Yuanyuan QinXiaoqing Zeng
Nov 14, 2020·Chemical Communications : Chem Comm·Shuguang ZhouTeck-Peng Loh
Mar 6, 2008·The Journal of Organic Chemistry·Thomas N Tekavec, Janis Louie
May 20, 2008·Organic Letters·Chunsong XiePeixin Xu
Jan 13, 2015·Journal of the American Chemical Society·Wen-Zhen ZhangTomislav Rovis

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