Examination of nature's favorite molecules reveals a striking preference for making carbon-heteroatom bonds over carbon-carbon bonds-surely no surprise given that carbon dioxide is nature's starting material and that most reactions are performed in water. Nucleic acids, proteins, and polysaccharides are condensation polymers of small subunits stitched together by carbon-heteroatom bonds. Even the 35 or so building blocks from which these crucial molecules are made each contain, at most, six contiguous C-C bonds, except for the three aromatic amino acids. Taking our cue from nature's approach, we address here the development of 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 we call "click chemistry". Click chemistry is at once defined, enabled, and constrained by a handful of nearly perfect "spring-loaded" reactions. The stringent criteria for a process to earn click chemistry status are described along with examples of the molecular frameworks that are easily made using this spartan, but powerful, synthetic strategy.

https://www.onlinelibrary.wiley.com/doi/pdf/10.1002/1521-3773%2820010601%2940%3A11%3C2004%3A%3AAID-ANIE2004%3E3.0.CO%3B2-5

Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Reduced transition metal colloids: a novel family of reusable catalysts

Betrachtet man die in der Natur am haufigsten vorkommenden Verbindungen, so fallt auf, dass die Bildung von Kohlenstoff-Heteroatom-Bindungen gegenuber der von Kohlenstoff-Kohlenstoff-Bindungen deutlich bevorzugt ist Da zum einen Kohlendioxid die Basisverbindung der Natur ist und andererseits das Medium naturlicher Reaktionen zumeist Wasser ist, uberrascht dies sicherlich nicht Nucleinsauren, Proteine und Polysaccharide sind polymere Kondensationsprodukte kleiner Untereinheiten, die durch Kohlenstoff-Heteroatom-Bindungen verknupft sind Sogar die etwa 35 Baueinheiten, aus denen diese essentiellen Verbindungen bestehen, enthalten nicht mehr als sechs aufeinander folgende C-C-Bindungen, sieht man einmal von den drei aromatischen Aminosauren ab Mit der Natur als Vorbild richteten wir unser Interesse auf die Entwicklung leistungsfahiger, gut funktionierender und selektiver Reaktionen fur die effiziente Synthese neuartiger nutzlicher Verbindungen sowie kombinatorischer Bibliotheken mittels Heteroatomverknupfungen (C-X-C) Diese Synthesestrategie nennen wir „Click-Chemie“ Click-Chemie ist durch eine Auswahl einiger weniger nahezu idealer Reaktionen charakterisiert, mit all ihren Grenzen und Moglichkeiten In diesem Beitrag werden zum einen die strengen Kriterien, die Reaktionen erfullen mussen, um die Bezeichnung „Click-Chemie“ zu verdienen, definiert, zum anderen werden Beispiele fur molekulare Strukturen gegeben, die mit dieser spartanischen, aber dennoch leistungsfahigen Synthesestrategie leicht hergestellt werden konnen

Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

Reḿi Auvergne,† Sylvain Caillol,† Ghislain David,*,† Bernard Boutevin,† and Jean-Pierre Pascault‡,§ †Institut Charles Gerhardt UMR CNRS 5253 Laboratoire Ingeńierie et Architecture Macromolećulaire, Ecole Nationale Supeŕieure de Chimie de Montpellier, 8 rue de l’Ecole Normale, 34296 Montpellier Cedex 05, France ‡INSA-Lyon, IMP, UMR5223, F-69621, Villeurbanne, France Universite ́ de Lyon, F-69622, Lyon, France

Biobased thermosetting epoxy: present and future.

Sequence-specific cross-linking of deoxyoligonucleotides via hybridization-triggered alkylation

We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions

Conformationally restricted arginine analogs

We describe a novel asymmetric approach using Staudinger chemistry to proline-derived spiro-β-lactams. A chiral group at C-4 of the acid chloride of proline directs the stereoselectivity of Staudin...

Novel Asymmetric Approach to Proline-Derived Spiro-β-lactams

Oxidation of thiols to disulfides with monochloro poly(styrenehydantoin) beads

The coordination chemistry of silver(I) with the nitrogen-bridged ligands (C6H5)2PN(R)P(C6H5)2 [R = H (dppa); R = CH3 (dppma)] has been investigated by 31P NMR and electrospray mass spectrometry (ESMS). Species observed by 31P NMR include Ag2(μ-dppa)2+, Ag2(μ-dppa)22+, Ag2(μ-dppa)32+, Ag2(μ-dppma)2+, Ag2(μ-dppma)22+, and Ag(η2-dppma)2+. Species observed by ESMS at low cone voltages were Ag2(dppa)22+, Ag2(dppa)32+, Ag2(dppma)22+, and Ag(dppma)2+. (C6H5)2PN(CH3)P(C6H5)2 showed a strong tendency to chelate, while (C6H5)2PN(H)P(C6H5)2 preferred to bridge. Differences in the bridging versus chelating behavior of the ligands are assigned to the Thorpe−Ingold effect, where the methyl group on nitrogen sterically interacts with the phenyl groups on phosphorus. The crystal structure of the three-coordinate dinuclear silver(I) complex {Ag2[(C6H5)2PN(H)P(C6H5)2]3}(BF4)2 has been determined. Bond distances include Ag−Ag = 2.812(1) A, Ag(1)−P(av) = 2.492(3) A, and Ag(2)−P(av) = 2.509(3) A. The compound crystallizes in...

Coordination Chemistry of Silver(I) with the Nitrogen-Bridged Ligands (C6H5)2PN(H)P(C6H5)2 and (C6H5)2PN(CH3)P(C6H5)2: The Effect of Alkylating the Nitrogen Bridge on Ligand Bridging versus Chelating Behavior

Thomas R. Webb

Papers

Sequence-specific cross-linking of deoxyoligonucleotides via hybridization-triggered alkylation

Conformationally restricted arginine analogs

Novel Asymmetric Approach to Proline-Derived Spiro-β-lactams

Oxidation of thiols to disulfides with monochloro poly(styrenehydantoin) beads

Coordination Chemistry of Silver(I) with the Nitrogen-Bridged Ligands (C6H5)2PN(H)P(C6H5)2 and (C6H5)2PN(CH3)P(C6H5)2: The Effect of Alkylating the Nitrogen Bridge on Ligand Bridging versus Chelating Behavior