A versatile living polymerization method for aromatic amides.

Nature Chemistry
Subhajit PalAndreas F M Kilbinger

Abstract

Polycondensation polymers typically follow step-growth kinetics assuming all functional groups are equally likely to react with one another. If the reaction rates with the chain end can be selectively accelerated, living polymers can be obtained. Here we report on two chlorophosphonium iodide reagents that have been synthesized from triphenylphosphine and tri(o-methoxyphenyl)phosphine. The former activates aromatic carboxylic acids as acid chlorides in the presence of secondary aromatic amines and the latter even in the presence of primary aromatic amines. These reagents allow p-aminobenzoic acid derivatives to form solution-stable activated monomers that polymerize in a living fashion in the presence of amine initiators. Other aryl amino acids and even dimers of aryl amino acids can be polymerized in a living fashion when slowly added to the phosphonium salt in the presence of an amine initiator. Diblock copolymers and triblock terpolymers of aryl amino acids can be prepared even in the presence of electrophilic functional groups.

References

Aug 15, 2002·Proceedings of the National Academy of Sciences of the United States of America·Bing GongLihua Yua
Jun 9, 2005·Journal of the American Chemical Society·Aya TanataniTsutomu Yokozawa
Apr 21, 2006·Organic Letters·Hannah M KönigAndreas F M Kilbinger
Jan 18, 2007·Journal of the American Chemical Society·Hannah M KönigAndreas F M Kilbinger
Mar 7, 2009·Magnetic Resonance in Chemistry : MRC·Nina C GonnellaDaniel L Norwood
Oct 16, 2010·The Journal of Organic Chemistry·Benoît BaptisteIvan Huc
Oct 9, 2012·Chemical Communications : Chem Comm·Jinxin CaoBing Gong
Aug 10, 2013·Science·Jean-François LutzMitsuo Sawamoto
Jan 17, 2014·Chemical Society Reviews·Helena LundbergHans Adolfsson
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jun 9, 2015·Journal of the American Chemical Society·Will R Gutekunst, Craig J Hawker
Nov 12, 2015·Chemical Reviews·Tsutomu Yokozawa, Yoshihiro Ohta
Sep 3, 2016·Methods in Enzymology·S J DawsonI Huc
Nov 1, 2017·Chemistry Central Journal·Antonella LeggioAngelo Liguori
Nov 22, 2017·Macromolecular Rapid Communications·Jean-François Lutz
Feb 20, 2018·Journal of the American Chemical Society·Subhajit PalAndreas F M Kilbinger
Mar 21, 2018·Nature Chemistry·Joseph M RogersIvan Huc
Sep 20, 2018·Journal of the American Chemical Society·Zixuan HuangJiangtao Xu
Nov 6, 2018·The Journal of Organic Chemistry·Ko UrushibaraAya Tanatani

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