Complete control of the chemoselectivity in catalytic carbene transfer reactions from ethyl diazoacetate: an N-heterocyclic carbene-Cu system that suppresses diazo coupling

Journal of the American Chemical Society
Manuel R FructosPedro J Pérez

Abstract

The complex IPrCuCl (1) catalyzes the transfer of the :CHCO2Et group from ethyl diazoacetate (EDA) to unsaturated and saturated substrates (olefins, amine, alcohols) with very high yields. In the absence of substrate, the complex 1 does not react with EDA to give the diazo coupling products (fumarate and maleate), a rare example in the field of metal-catalyzed diazocompounds decomposition.

References

May 11, 2000·Organic Letters·D S ClyneT V RajanBabu
Sep 6, 2001·Journal of the American Chemical Society·M T PowellK Burgess
Dec 26, 2001·Chemical Reviews·Didier BourissouGuy Bertrand
Oct 5, 2002·Science·István E MarkóJean-Paul Declercq

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Citations

Feb 8, 2007·Chemical Communications : Chem Comm·Iris Aviv, Zeev Gross
May 26, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Igor V ShishkovPeter Hofmann
Sep 18, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Jaime A FloresH V Rasika Dias
May 21, 2010·Chemical Communications : Chem Comm·Dehui WangChunying Duan
Apr 20, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Cécilia A CitadelleCatherine S J Cazin
Jul 9, 2016·The Journal of Organic Chemistry·Kankanala Ramakrishna, Chinnappan Sivasankar
Dec 15, 2015·Chemical Society Reviews·Lu Liu, Junliang Zhang
Jan 8, 2016·Organic & Biomolecular Chemistry·Thomas J ThomasMichael G Coleman
Jul 2, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·René PretoriusMartin Albrecht
Oct 7, 2016·Chemical Communications : Chem Comm·RahulKumar Rajmani SinghRai-Shung Liu
Dec 22, 2006·Chemistry : a European Journal·Vanesa LilloElena Fernández
Feb 20, 2009·Organic & Biomolecular Chemistry·Zhiyong WangJie Wu
Jul 23, 2005·Angewandte Chemie·Manuel R FructosPedro J Pérez
Jul 17, 2015·Chemistry : a European Journal·Holger BraunschweigChristine Werner
Feb 15, 2013·Chemical Society Reviews·Dennis Gillingham, Na Fei
Jan 5, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Xiaoyu YueYu Lan
Apr 25, 2020·Chemistry : a European Journal·Juan Diego PizarroPedro J Pérez
Nov 27, 2020·Chemistry : a European Journal·Steffen A FöhrenbacherUdo Radius
Feb 18, 2009·Organic Letters·Jianming LiuChungu Xia
Jul 11, 2009·Chemical Reviews·Silvia Díez-GonzálezSteven P Nolan
Aug 14, 2008·Chemical Reviews·M Mar Díaz-Requejo, Pedro J Pérez
Jul 26, 2008·Chemical Reviews·David J GorinF Dean Toste
Nov 3, 2020·Chemical Reviews·Mauro MatoAntonio M Echavarren
Feb 21, 2018·Journal of the American Chemical Society·Judit Oliver-MeseguerAvelino Corma
May 4, 2006·Journal of the American Chemical Society·Barry M Trost, Guangbin Dong
Dec 30, 2006·The Journal of Organic Chemistry·Hélène LebelSteven P Nolan

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