2001 · Angewandte Chemie International Edition · 13,077 citations
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.
2012 · Chemical Reviews · 2,527 citations
ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTChemistry and Biology Of Multicomponent ReactionsAlexander Dömling*†‡, Wei Wang†§, and Kan Wang†View Author Information† Department of Pharmaceutical Sciences, University of Pittsburgh, Biomedical Science Tower 3, Suite 10019, 3501 Fifth Avenue, Pittsburgh, Pennsylvania 15261, United States‡ Chair of Drug Design, Antonius Deusinglaan 1, 9713 AV Groningen, The Netherlands§ Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, and School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, P. R. China*E-mail: [email protected]. Fax: (+)412-383-5298.Cite this: Chem. Rev. 2012, 112, 6, 3083–3135Publication Date (Web):March 22, 2012Publication History Received23 July 2010Published online22 March 2012Published inissue 13 June 2012https://pubs.acs.org/doi/10.1021/cr100233rhttps://doi.org/10.1021/cr100233rreview-articleACS PublicationsCopyright © 2012 American Chemical SocietyRequest reuse permissionsArticle Views31588Altmetric-Citations1987LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Inhibitors,Peptides and proteins,Reaction products,Receptors,Scaffolds Get e-Alerts