4572-12-7Relevant articles and documents
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.
Synthesis and 13C NMR spectroscopy of 13C-labeled α,ω-diphenylpolyynes
Tykwinski, Rik R.,Luu, Thanh
, p. 1915 - 1922 (2012/08/07)
The synthesis of three 13C-labeled α,ω- diphenylpolyynes is described. The known positions of the labeled carbon atoms allow assignment of the resonances in the 13C NMR spectra and identification of trends in the chemical shifts. Geo
Synthesis of diynes and tetraynes from in situ desilylation/dimerization of acetylenes
Heuft, Matthew A.,Collins, Shawn K.,Yap, Glenn P. A.,Fallis, Alex G.
, p. 2883 - 2886 (2007/10/03)
(equation presented) An efficient method for the in situ desilylation/oxidative dimerization of (trialkylsilyl)acetylenes is described. This protocol avoids the complications encountered with sensitive diynes by eliminating the deprotection and isolation steps. Various aromatic and alkyl diynes and tetraynes can be synthesized in a straightforward manner in good yields (82-99%) from TIPS-protected acetylenes. This method facilitates the efficient synthesis of novel tetrayne-bridged acetylenic cyclophanes 6 and 7 in a direct manner.