4572-12-7Relevant 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.
Mori-Hiyama versus hay coupling for higher polyynes
Gulia, Nurbey,Osowska, Karolina,Pigulski, Bartlomiej,Lis, Tadeusz,Galewski, Zbigniew,Szafert, Slawomir
experimental part, p. 4819 - 4830 (2012/10/18)
Dimerizations of C4 precursors RCa=CCa=CTMS [R = C 6H5 (1), p-CH3C6H5, (2), 4-n-C5H11C6H4 (3), C 6H9 (4), p-CH3O
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
One-pot formation and derivatization of di- and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement
Luu, Thanh,Morisaki, Yasuhiro,Cunningham, Nina,Tykwinski, Rik R.
, p. 9622 - 9629 (2008/03/15)
(Chemical Equation Presented) A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement is used to gene
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.
One-pot desilylation/dimerization of ethynyl- and butadiynyltrimethylsilanes. Synthesis of tetrayne-linked dehydrobenzoannulenes
Haley, Michael M.,Bell, Michael L.,Brand, Stephen C.,Kimball, David B.,Pak, Joshua J.,Wan, W. Brad
, p. 7483 - 7486 (2007/10/03)
Addition of K2CO3 to standard Eglinton coupling conditions effects a one-pot desilylation/dimerization reaction of alkynyltrimethylsilanes. Use of this procedure on substituted phenylbutadiynylsilanes ultimately leads to the formation of dehydrobenzoannulenes possessing an unprecedented number of acetylene linkers.
On the Regio- and Stereoselectivity of Nucleophilic Thiol Additions to Polyines
Zschunke, A.,Muegge, C.,Hintzsche E.,Schroth, W.
, p. 141 - 146 (2007/10/02)
Nucleophilic thiophenol additions to α,ω-diphenyl polyines Ph-(CC)n-Ph (n = 2-4) (1-3) take a regio- and stereoselective course.The welldefined, crystalline addition products bind the phenylthio group in terminal position of the aliphatic chain, the re
