1217554-49-8Relevant academic research and scientific papers
One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes
Andrade, Camila B.,Carvalho, Diego B.,Trefzger, Ozildéia S.,Kassab, Najla M.,Guerrero, Palimécio G.,Barbosa, Sandro L.,Shiguemoto, Cristiane Y. K.,Baroni, Adriano C. M.
, p. 696 - 704 (2019/01/04)
A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.
Copper-catalyzed decarboxylative cross-coupling of propiolic acids and terminal alkynes
Yu, Miao,Pan, Delin,Jia, Wei,Chen, Wei,Jiao, Ning
supporting information; experimental part, p. 1287 - 1290 (2010/04/27)
A copper-catalyzed decarboxylative cross-coupling reaction of propiolic acids with terminal alkynes is developed leading to unsymmetric 1,3-conjugated diynes under mild conditions. This method provides a novel decarboxylative cross-coupling for sp-sp bond formation. Compared to organic halides, only carbon dioxide is produced as by-products in this approach.
