An inexpensive and recyclable silver-foil catalyst for the cyclopropanation of alkenes with diazoacetates under mechanochemical conditions

Angewandte Chemie
Longrui ChenJames Mack

Abstract

The diastereoselective cyclopropanation of various alkenes with diazoacetate derivatives can be achieved under mechanochemical conditions using metallic silver foil and a stainless-steel vial and ball system. This solvent-free method displays analogous reactivity and selectivity to solution-phase reactions without the need for slow diazoacetate addition or an inert atmosphere. The heterogeneous silver-foil catalyst system is easily recyclable without any appreciable loss of activity or selectivity being observed. The cyclopropanation products were obtained with excellent diastereoselectivities (up to 98:2 d.r.) and in high yields (up to 96 %).

References

Feb 19, 2002·Chemical Reviews·Michael P. Doyle, David C. Forbes
Aug 14, 2003·Chemical Reviews·Huw M L Davies, Rohan E J Beckwith
Mar 17, 2004·Proceedings of the National Academy of Sciences of the United States of America·Huw M L Davies, Qihui Jin
Mar 18, 2004·Chemical Society Reviews·Gerhard Maas
Dec 22, 2004·The Journal of Organic Chemistry·Huw M L Davies, Rohan E J Beckwith
Jul 1, 2005·Organic Letters·Huw M L Davies, Abbas M Walji
Apr 20, 2007·Journal of the American Chemical Society·Janelle L Thompson, Huw M L Davies
Aug 13, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Oleg N ShishilovLuís Miguel Martínez-Prieto
May 21, 2010·Beilstein Journal of Organic Chemistry·Franziska BernhardtBernd Ondruschka
Sep 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nina Kann
Mar 10, 2011·Chemical Society Reviews·Achim StolleBernd Ondruschka
Sep 6, 2011·Chemical Society Reviews·Stuart L JamesDaniel C Waddell
May 15, 2012·Accounts of Chemical Research·Huw M L Davies, Yajing Lian
May 11, 2013·Chemical Society Reviews·Guan-Wu Wang
Nov 21, 2013·Organic Letters·Kathryn M ChepigaHuw M L Davies
May 16, 2014·Chemistry : a European Journal·Andreas Bergmann, Oliver Reiser
Nov 20, 2014·Faraday Discussions·David W Peters, Richard G Blair
Feb 11, 2015·Journal of the American Chemical Society·Jean-Louis DoTomislav Friščić

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Citations

Jan 13, 2017·The Journal of Organic Chemistry·José G Hernández, Carsten Bolm
Jan 21, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cristina Mottillo, Tomislav Friščić
Apr 29, 2016·Chemical Communications : Chem Comm·Gao-Feng ZhaCheng-Pan Zhang
Apr 27, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Jingyi WangFelipe García
May 8, 2018·Angewandte Chemie·Alexander G TskhovrebovAlois Fürstner
Oct 24, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas E ShawTitel Jurca
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Agota A Gečiauskaitė, Felipe García
Jul 12, 2019·Angewandte Chemie·Tomislav FriščićHatem M Titi
Mar 30, 2020·ChemSusChem·Gandrath DayakerTomislav Friscic
May 22, 2018·Chemical Science·Joseph L HowardDuncan L Browne
Sep 22, 2020·Chemical Science·Abhijnan SarkarFabio Ragaini
Aug 25, 2017·Chemistry : a European Journal·José G Hernández
Oct 4, 2017·Chemical Science·Joel M Andersen, James Mack
Jun 25, 2021·Frontiers in Chemistry·Adam A L MichalchukVladimir V Boldyrev
Feb 6, 2017·ACS Central Science·Jean-Louis Do, Tomislav Friščić

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