Silver-catalyzed decarboxylative alkynylation of aliphatic carboxylic acids in aqueous solution.

J Am Chem Soc

College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230039, P.R. China.

Published: September 2012

AI Article Synopsis

  • C(sp(3))-C(sp) bond formations are crucial in chemistry and material sciences, highlighting the need for effective methods in this area.
  • The study presents a radical-mediated catalytic method using AgNO(3) as a catalyst and K(2)S(2)O(8) as an oxidant for C(sp(3))-C(sp) cross-coupling in mild aqueous conditions.
  • This method allows for efficient decarboxylative alkynylation of various aliphatic carboxylic acids, demonstrating high compatibility with functional groups and remarkable chemo- and stereoselectivity.

Article Abstract

C(sp(3))-C(sp) bond formations are of immense interest in chemistry and material sciences. We report herein a convenient, radical-mediated and catalytic method for C(sp(3))-C(sp) cross-coupling. Thus, with AgNO(3) as the catalyst and K(2)S(2)O(8) as the oxidant, various aliphatic carboxylic acids underwent decarboxylative alkynylation with commercially available ethynylbenziodoxolones in aqueous solution under mild conditions. This site-specific alkynylation is not only general and efficient but also functional group compatible. In addition, it exhibits remarkable chemo- and stereoselectivity.

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Source
http://dx.doi.org/10.1021/ja306638sDOI Listing

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