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 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.
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.
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.
