Journal ArticleDOI
Schwefel(VI)-fluorid-Austausch (SuFEx): Eine weitere gute Anwendung für die Click-Chemie
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This article is published in Angewandte Chemie.The article was published on 2014-09-01. It has received 149 citations till now.read more
Citations
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Late-stage fluorination: fancy novelty or useful tool?
TL;DR: It is outlined how an improved understanding of the bonding interactions of fluoride could lead to a new class of mild fluorinating reagents and a range of functional-group-tolerant reactions.
Journal ArticleDOI
Lysine-Targeting Covalent Inhibitors.
TL;DR: The key principles for inhibitor design are reviewed, historical examples are given, and recent developments are presented that demonstrate the potential of lysine targeting for future drug discovery.
Journal ArticleDOI
A Heck–Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry
TL;DR: The β-arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions, making these rather simple cores attractive for covalent drug discovery.
Journal ArticleDOI
Facile Synthesis of Sequence-Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions
TL;DR: The orthogonal sulfur-fluoride exchange reaction (SuFEx) and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) are employed to synthesize sequence-regulated synthetic polymers that afford monodispersed sequence-defined oligomers with a high degree of structural diversity.
Journal ArticleDOI
SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts.
Hua Wang,Feng Zhou,Feng Zhou,Gerui Ren,Gerui Ren,Qinheng Zheng,Hongli Chen,Bing Gao,Liana M. Klivansky,Yi Liu,Bin Wu,Qingfeng Xu,Jianmei Lu,K. Barry Sharpless,Peng Wu +14 more
TL;DR: The SuFEx-based polysulfonate formation reaction exhibited excellent efficiency and functional group tolerance, producing polys sulfuronates with a variety of side chain functionalities in >99 % conversion within 10 min to 1 h.
References
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A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
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Click Chemistry: Diverse Chemical Function from a Few Good Reactions.
TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
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Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
TL;DR: A novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported, and the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1, 3-dipoles entering the reaction.
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1,3-Dipolar Cycloadditions. Past and Future†
TL;DR: In contrast to the very large number of special methods applicable to syntheses in the heterocyclic series, relatively few general methods are available as discussed by the authors, and the 1,3-dipolar addition offers a remarkably wide range of utility in the synthesis of five-membered heterocycles.
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A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems
TL;DR: A strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.