Silver-catalyzed decarboxylative alkynylation of aliphatic carboxylic acids in aqueous solution.
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.
College of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230039, P.R. China.
Xuesong
X
Liu
Zhentao
Z
Wang
Xiaomin
X
Cheng
Chaozhong
C
Li
D000480:Alkynes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D012996:Solutions; D014867:Water / Q000737:chemistry*
D000480:Alkynes; D002264:Carboxylic Acids; D007462:Iodobenzenes; D007463:Iodobenzoates; D012996:Solutions; D014867:Water; C476101:o-iodoxybenzoic acid; D012834:Silver