1394826-25-5Relevant articles and documents
Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes
Huang, Liangbin,Olivares, Astrid M.,Weix, Daniel J.
, p. 11901 - 11905 (2017)
A new method for the synthesis of terminal and internal alkynes from the nickel-catalyzed decarboxylative coupling of N-hydroxyphthalimide esters and bromoalkynes is presented. This reductive cross-electrophile coupling is the first to use a C(sp)?X electrophile, and appears to proceed via an alkynylnickel intermediate. The internal alkyne products are obtained in yields of 41–95 % without the need for a photocatalyst, light, or a strong oxidant. The reaction displays a broad scope of carboxylic acid and alkyne coupling partners, and can tolerate an array of functional groups, including carbamate NH, halogen, nitrile, olefin, ketone, and ester moieties. Mechanistic studies suggest that this process does not involve an alkynylmanganese reagent and instead proceeds through nickel-mediated bond formation.
Silver-catalyzed decarboxylative alkynylation of aliphatic carboxylic acids in aqueous solution
Liu, Xuesong,Wang, Zhentao,Cheng, Xiaomin,Li, Chaozhong
supporting information, p. 14330 - 14333 (2012/10/30)
C(sp3)-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(sp3)-C(sp) cross-coupling. Thus, with AgNO3 as the catalyst and K2S2O8 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.