1725-82-2Relevant articles and documents
Reactions of Terminal Alkynes with Bis(trimethylsilyl) Peroxide and Zinc(II) Iodide: A Convenient Method for the Preparation of 1-Iodo-1-alkynes
Ricci, A.,Taddei, M.,Dembech, P.,Guerrini, A.,Seconi, G.
, p. 461 - 463 (1989)
A convenient, mild, and general one-pot synthesis of 1-iodo-1-alkynes from terminal acetylenes, bis(trimethylsilyl) peroxide, and zinc(II) iodide in the presence of n-butyllithium is reported.
A simple convenient method for the synthesis of 1-iodoalkynes
Narayana Rao,Periasamy
, p. 2295 - 2299 (1995)
Reaction of terminal alkynes with ethylmagnesium bromide in THF followed by the addition of iodine in THF gives 1-iodoalkynes in excellent yields (90-96%).
A New Multicomponent Multicatalyst Reaction (MC)2R: Chemoselective Cycloaddition and Latent Catalyst Activation for the Synthesis of Fully Substituted 1,2,3-Triazoles
Yamamoto, Kosuke,Bruun, Theodora,Kim, Jung Yun,Zhang, Lei,Lautens, Mark
supporting information, p. 2644 - 2647 (2016/06/15)
A multicomponent multicatalyst reaction (MC)2R for constructing fully substituted 1,2,3-triazoles is reported. An application of chemoselectivity and latent catalysis in a sequence of multicatalytic reactions confers control over a number of undesired processes, where all of the reagents coexist in the same reaction vessel. The sequence of a chemoselective copper-catalyzed azide alkyne cycloaddition followed by a palladium/copper-catalyzed Sonogashira cross-coupling afforded 1,2,3-triazoles regioselectively with good to high yields and a broad scope.
FUNGICIDAL PENFLUFEN MIXTURES
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, (2014/04/03)
The invention relates to mixtures comprising penflufen, to the use of these mixtures for protecting industrial materials and to a method for treating industrial materials with the penflufen mixtures.
Synthesis of 5-Iodo-1,2,3-triazoles from organic azides and terminal alkynes: Ligand acceleration effect, substrate scope, and mechanistic insights
Barsoum, David N.,Brassard, Christopher J.,Deeb, Jason H. A.,Okashah, Najeah,Sreenath, Kesavapillai,Simmons, J.Tyler,Zhu, Lei
, p. 2372 - 2386 (2013/09/23)
An improved method has been developed for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes by a reaction mediated by copper(I) and iodinating agents generated in situ. The major methodological advance of the current procedure is that it provides a high conversion and good iodo/proto selectivity with a broad range of substrates without using an excess of the alkyne, which was required in the previous method. The use of an accelerating ligand is essential to the success of reactions involving unreactive azides or alkynes. New mechanistic insights are provided, including the confirmation that a 1-iodoalkyne is formed as a key intermediate under the established conditions for the reaction.
Synthesis of 1,2,3-triazole-fused heterocycles via Pd-catalyzed cyclization of 5-iodotriazoles
Schulman, Jacqueline M.,Friedman, Adam A.,Panteleev, Jane,Lautens, Mark
supporting information; experimental part, p. 55 - 57 (2012/01/05)
A convenient approach toward polycyclic frameworks containing fused 1,2,3-triazoles is described. The synthesis consists of a Cu-catalyzed cycloaddition and an intramolecular Pd-catalyzed direct arylation or Heck reaction, and affords the products in good to excellent yields.
Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates
Passiniemi, Mikko,Koskinen, Ari M. P.
experimental part, p. 1774 - 1783 (2011/05/04)
A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η3-allylpalladium intermediate.
Synthesis of γ-monofluorinated goniothalamin analogues via regio- and stereoselective ring-opening hydrofluorination of epoxide
Chen, Jun-Ling,Zheng, Feng,Huang, Yangen,Qing, Feng-Ling
scheme or table, p. 6525 - 6533 (2011/10/03)
A stereoselective synthesis of the biologically interesting γ-monofluorinated goniothalamin analogue 2a was described. The features of the synthesis included regioselective reduction of the unprotected hydroxypropynyl moiety of compound 10 by Red-Al, asymmetric Sharpless epoxidation of allyl alcohol 11, and regio- and stereoselective ring-opening hydrofluorination of the hydroxypropynyl epoxide 14 with Et3N? 3HF in high ee and dr. The chiral hydroxypropynyl fluorohydrin 15 was used as a valuable building block for preparation of a range of γ-monofluorinated α,β-unsaturated δ-lactones.
Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide
Rajender Reddy,Venkateshwar,Uma Maheswari,Santhosh Kumar
supporting information; experimental part, p. 2170 - 2173 (2010/06/14)
An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield.
Synthesis of diacetylene-containing peptide building blocks and amphiphiles, their self-assembly and topochemical polymerization in organic solvents
Jahnke, Eike,Weiss, Jan,Neuhaus, Sonja,Hoheisel, Tobias N.,Frauenrath, Holger
experimental part, p. 388 - 404 (2009/08/07)
A series of functional iodoacetylenes was prepared and converted into the corresponding diacetylene-substituted amino acids and peptides via Pd/Cu-promoted sp-sp carbon cross-coupling reactions. The unsymmetrically substituted diacetylenes can be incorporated into oligopeptides without a change in the oligopeptide strand's directionality. Thus, a series of oligopeptide-based, amphiphilic diacetylene model compounds was synthesized, and their self-organization as well as their UV-induced topochemical polymerizability was investigated in comparison to related polymer-substituted macromonomers. Solution-phase IR spectroscopy, gelation experiments, and UV spectroscopy helped to confirm that a minimum of five N-H...O=C hydrogen-bonding sites was required in order to obtain reliable aggregation into stable β-sheet-type secondary structures in organic solvents. Furthermore, the non-equidistant spacing of these hydrogen-bonding sites was proven to invariably lead to β-sheets with a parallel β-strand orientation, and the characteristic IR-spectroscopic signatures of the latter in organic solution was identified. Scanning force micrographs of the organogels revealed that compounds with six hydrogen-bonding sites gave rise to high aspect ratio nanoscopic fibrils with helical superstructures but, in contrast to the related macromonomers, did not lead to uniform supramolecular polymers. The UV-induced topochemical polymerization within the β-sheet aggregates was successful, proving parallel β-strand orientation and highlighting the effect of the number and pattern of N-H...O=C hydrogen-bonding sites as well as the hydrophobic residue in the molecular structure on the formation of higher structures and reactivity.
