A Versatile Approach to Dynamic Amide Bond Formation with Imine Nucleophiles

Chemistry : a European Journal
Huseyin ErguvenBruce A Arndtsen

Abstract

Dynamic covalent chemistry has rapidly become an important approach to access supramolecular structures. While the products generated in these reactions are held together by covalent bonds, the reversible nature of the transformations can limit the utility of many these systems in creating robust materials. We describe herein a method to form stable and commonly employed amide bonds by exploiting the reversible coupling of imines and acyl chlorides. The reaction employs easily accessible reagents, is dynamic under ambient conditions, without catalysts, and can be trapped with simple hydrolysis. This offers an approach to create broad families of amide products under thermodynamic control, including the selective formation of amide macrocycles or polymers.

References

Mar 10, 2001·Nature·S R WhiteS Viswanathan
Mar 30, 2002·Science·Jean-Marie Lehn
Jul 18, 2002·Nature Reviews. Drug Discovery·Olof Ramström, Jean-Marie Lehn
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Mar 11, 2004·Chemical Reviews·Bruce E MaryanoffCynthia A Maryanoff
Jul 30, 2005·Chemistry : a European Journal·Michał J Chmielewski, Janusz Jurczak
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Aug 30, 2007·Journal of the American Chemical Society·C Scott Hartley, Jeffrey S Moore
Jan 3, 2009·Nature Nanotechnology·Richard J WilliamsRein V Ulijn
Jul 23, 2009·Journal of the American Chemical Society·Nickeisha A StephensonShannon S Stahl
Dec 17, 2009·Chemical Reviews·Georgios C Vougioukalakis, Robert H Grubbs
Jul 3, 2010·Current Opinion in Biotechnology·Jan W Sadownik, Rein V Ulijn
Dec 22, 2010·Journal of the American Chemical Society·Karolina Osowska, Ognjen Š Miljanić
Apr 21, 2011·Journal of Medicinal Chemistry·Stephen D Roughley, Allan M Jordan
Sep 13, 2011·Chemical Society Reviews·Emilie MoulinNicolas Giuseppone
Feb 9, 2012·Chemical Society Reviews·Matthew E Belowich, J Fraser Stoddart
Jun 9, 2012·Organic Letters·Thanh Binh NguyenAli Al-Mourabit
Jul 24, 2012·Chemical Society Reviews·Xiao FengDonglin Jiang
Aug 9, 2012·Chemical Reviews·Dan-Wei ZhangZhan-Ting Li
Oct 13, 2012·Chemical Society Reviews·San-Yuan Ding, Wei Wang
Nov 15, 2012·Accounts of Chemical Research·Steven D BullTony D James
Jan 29, 2013·Angewandte Chemie·Alois Fürstner
Apr 13, 2013·Chemical Society Reviews·Christopher J Kloxin, Christopher N Bowman
Jun 12, 2013·Chemical Society Reviews·Yinghua JinWei Zhang
Aug 22, 2013·Accounts of Chemical Research·Santiago V Luis, I Alfonso
Oct 18, 2013·Chemical Society Reviews·Samuel P BlackArtur R Stefankiewicz
Apr 11, 2014·Journal of the American Chemical Society·Yves RuffNicolas Giuseppone
Apr 18, 2014·Accounts of Chemical Research·Yinghua JinWei Zhang
Apr 25, 2014·The Journal of Organic Chemistry·Liliana Becerra-FigueroaDiego Gamba-Sánchez
May 6, 2015·Chemical Society Reviews·Nabarun RoyJean-Marie Lehn
Jul 17, 2015·Chemical Reviews·Yan Zhang, Mihail Barboiu
Jan 29, 2016·The Journal of Organic Chemistry·Vicente Martí-CentellesSantiago V Luis
Jul 30, 2016·Journal of the American Chemical Society·Laure V KayserBruce A Arndtsen
Oct 21, 2016·Chemistry : a European Journal·Jevgenijs TjutrinsBruce A Arndtsen
Dec 10, 2016·Journal of the American Chemical Society·Peter J WallerOmar M Yaghi
Mar 4, 2017·Science·Christian S Diercks, Omar M Yaghi
May 5, 2017·Journal of the American Chemical Society·David A LeighXiaokang Zhu
May 12, 2017·Chemical Reviews·Peng Wu, Thomas E Nielsen
Aug 23, 2017·Chemical Society Reviews·Matthew J Webber, Robert Langer
Jul 13, 2018·Journal of the American Chemical Society·Peter J WallerOmar M Yaghi
Jan 25, 2019·Accounts of Chemical Research·Sébastien Ulrich
Apr 10, 2019·Angewandte Chemie·Avinash S BhatMichael Mastalerz
Jul 19, 2019·Journal of the American Chemical Society·Jeong-Min SeoJong-Beom Baek

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Citations

Sep 16, 2021·Journal of the American Chemical Society·Filip Van LijsebettenFilip E Du Prez

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