Click synthesis

Leventis N, Sadekar A, Chandrasekaran N, Sotiriou-Leventis C (2010) Click synthesis of monolithic silicon carbide aerogels from poly acrylonitrile-coated 3D silica networks. Chem Mater 22 2790-2803 Boday D J, DeFriend K A, Wilson K V Jr, Coder D, Loy D A (2(X)8) Formation of polycyanoacrylate-sUica nanocomposites by chemical vapor deposition of cyanoacrylates on aerogels. Chem Mater 20 2845-2847 Boday D J, Stover R J, Muriithi B, Keller M W, Wertz J T, DeFriend Obrey K A, Loy D A (2009) Strong, low density nanocomposites by chemical vapor depositim and polymerization of cyanoacrylates on aminated siUca aerogels. ACS Appl Mater Interfaces 1 1364—1369... 

F. Alonso, Y. Moglie, G. Radivoy, M. Yus, / Org. Chem. 2011, 76, 8394-8405. Multicomponent click synthesis of 1,2,3-triazoles from epoxides in water catalyzed by copper nanoparticles on activated carbon. 

Type of reaction C-N and C-C bond formation Reaction conditions Methanol, room temperature Synthetic strategy One-pot multi-component click synthesis Catalyst CU2O... 

Keywords Alkyl halides, alkynes, sodium azide, CU2O, methanol, room temperature, multi-component reaction, click synthesis, heterocycles, substituted 5-alkynyl 1,2,3-triazoles... 

Alonso, F., Moglie, Y., Radivoy, G., and Yus, M. (2012). Copper-catalysed multicomponent click synthesis of 5-aUcynyl 1,2,3-triazoles under ambient temperature. Synlett, 23, 2179-2182. 

In modifications of the click synthesis of 1,2,3-triazoles, enol ethers (esters), or enamines have been introduced as alkyne equivalents in the thermal cycloaddition with azides [496]. Primarily, 4,5-dihydro-l,2,3-triazoles 29 are formed, which are transformed to the triazoles 27 by HX-elimination. 

Liu S, Muller P, Takase MK, Swager TM (2011) Click synthesis of heteroleptic tris-cyclometalated iridium(III) complexes Cu(I) triazolide intermediates as transmetalating. Inoig Chem 50 7598-7609... 

Li H, Yao Y, Han H, Zhan J (2009) Triazole-ester modified silver nanoparticles click synthesis and Cd colorimetric sensing. Chem Commun 4812 814... 

Li H, Zheng Q, Han C (2010) Click synthesis of Podand triazole-linked gold nanoparticles as highly selective and sensitive colorimetric probes for lead(II) ions. Analyst 135 1360-1364... 

The strategic bond is disconnected by just clicking with the mouse on it. A suitable synthesis precursor is then generated automatically by WODCA by adding appropriate atoms or groups to the open valences. 

Thomson . Click Organic Interactive to use a web-based palette to design a synthesis of alkyl halides, beginning with alcohols. 

Scheme 18 Click chemistry synthesis of 1,4-disubstituted triazoles...

Xiao CS, Zhao CW, He P, Tang ZH, Chen XS, Jing XB (2010) Facile synthesis of glycopo-lypeptides by combination of ring-opening polymerization of an alkyne-substituted N-carboxyanhydride and click glycosylation . Macromol Rapid Commun 31 991-997... 

By combining several click reactions, click chemistry allows for the rapid synthesis of useful new compounds of high complexity and combinatorial libraries. The 2-type reaction of the azide ion with a variety of epoxides to give azido alcohols has been exploited extensively in click chemistry. First of all, azido alcohols can be converted into amino alcohols upon reduction.70 On the other hand, aliphatic azides are quite stable toward a number of other standard organic synthesis conditions (orthogonality), but readily undergo 1,3-dipolar cycloaddition with alkynes. An example of the sequential reactions of... 

The use of click chemistry is a promising strategy as a postsynthetic ligation for nucleic acids in order to circumvent the time-consuming synthesis of phosphoramidites as DNA building blocks [31, 32]. This is particularly relevant for several fluorophores that are unstable under the acidic, oxidative, or basic conditions of automated DNA phosphoramidite chemistry and DNA workup. 

Another example of fluorescence intensity modulation in cou-marins is the 3-azido substitution that quenches the fluorescence completely. These compounds are used as starting material for the synthesis of fluorescent triazolocoumarins by click chemistry [31], Interestingly, the fluorescence of some coumarins depends strongly on the solvent. This is the case for 7-alkoxycoumarins that have been used as probes for microenvironments [32], 7-hydroxycoumarin that is pH sensitive, and 7-NR2 substituted coumarins such as coumarin 120 whose quantum yield is reduced in nonpolar solvents due to a change in the 3D structure [33],... 

This section presents selected examples of the use of zeolites and related porous materials for transformations of carbohydrates, that fall beyond the scope of the previous paragraphs. They include the use of zeolites in click chemistry and in a variety of reactions, including the synthesis of anhydro sugars, cyclization, elimination, and addition reactions to the carbonyl group. 

F. Perez-Balderas, J. Morales-Sanfrutos, F. Hemandez-Mateo, J. Isac-Garcia, and F. Santoyo-Gonzalez, Click multivalent homogeneous neoglycoconju-gates—Synthesis and evaluation of their binding affinities, Ear. J. Org. Chem., 2009 (2009) 2441-2453. 

G. Pourceau, A. Meyer, J.-J. Vasseur, and F. Morvan, Combinatorial and automated synthesis of phosphodiester galactosyl cluster on solid support by click chemistry assisted by microwaves, J. Org. Chem., 73 (2008) 6014—6017. 

Hiki S, Kataoka K (2007) A facile synthesis of azido-terminated heterobifunctional poly (ethylene glycol)s for click conjugation. Bioconjug Chem 18 2191-2196... 

Hiki S, Kataoka K (2010) Versatile and selective synthesis of click chemistry compatible heterobifunctional poly(ethylene glycol)s possessing azide and alkyne functionalities. Bioconjug Chem 21 248-254... 

Click chemistry refers to the reaction between an azido functional group and an alkyne to form a [3 + 2] cycloaddition product, a 5-membered triazole ring. This reaction has been used for many years in organic synthesis to form heterocyclic rings. Normally, the click reaction requires high temperatures, and this was the main reason that it was not used as a bioconjugation tool. However, it was discovered that in aqueous solutions and in the presence of Cu(I), the reaction kinetics are dramatically accelerated to provide high yields even at room temperature and ambient pressures (Rostovtsev et al., 2002 Tornoe et al., 2002 Sharpless et al., 2005). 

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