Carboxylic Acids as Substrates in Homogeneous CatalysisLukas J. Gooßen, Nuria Rodríguez, Käthe Gooßen|Angewandte Chemie International Edition|2008 In organic molecules carboxylic acid groups are among the most common functionalities. Activated derivatives of carboxylic acids have long served as versatile connection points in derivatizations and in the construction of carbon frameworks. In more recent years numerous catalytic transformations have been discovered which have made it possible for carboxylic acids to be used as building blocks without the need for additional activation steps. A large number of different product classes have become accessible from this single functionality along multifaceted reaction pathways. The frontispiece illustrates an important reason for this: In the catalytic cycles carbon monoxide gas can be released from acyl metal complexes, and gaseous carbon dioxide from carboxylate complexes, with different organometallic species being formed in each case. Thus, carboxylic acids can be used as synthetic equivalents of acyl, aryl, or alkyl halides, as well as organometallic reagents. This review provides an overview of interesting catalytic transformations of carboxylic acids and a number of derivatives accessible from them in situ. It serves to provide an invitation to complement, refine, and use these new methods in organic synthesis.
Late Transition Metal-Catalyzed Hydroamination and HydroamidationADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTLate Transition Metal-Catalyzed Hydroamination and HydroamidationLiangbin Huang, Matthias Arndt, Käthe Gooßen, Heinrich Heydt, and Lukas J. Gooßen*View Author Information Department of Chemistry, TU Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern, Germany*Tel.: (+49) 631-205-2046. Fax: (+49) 631-205-3921. E-mail: [email protected]Cite this: Chem. Rev. 2015, 115, 7, 2596–2697Publication Date (Web):February 27, 2015Publication History Received20 September 2012Published online27 February 2015Published inissue 8 April 2015https://pubs.acs.org/doi/10.1021/cr300389uhttps://doi.org/10.1021/cr300389ureview-articleACS PublicationsCopyright © 2015 American Chemical SocietyRequest reuse permissionsArticle Views29561Altmetric-Citations887LEARN 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:Amines,Catalysts,Cyclization,Hydrocarbons,Organic reactions Get e-Alerts
Carbonsäuren als Substrate in der homogenen KatalyseAbstract In organischen Molekülen zählen Carbonsäuregruppen zu den häufigsten Funktionalitäten. Seit langem dienen aktivierte Derivate der Carbonsäuren als vielseitige Anknüpfungspunkte bei Derivatisierungen und beim Aufbau von Kohlenstoffgerüsten. In den letzten Jahren sind zahlreiche katalytische Transformationen entdeckt worden, mit deren Hilfe Carbonsäuren ohne zusätzlichen Aktivierungsschritt direkt als Bausteine nutzbar werden. Über vielfältige Reaktionspfade wurde so aus dieser einzelnen Funktionalität eine große Zahl unterschiedlicher Produktklassen zugänglich. Der Vortitel illustriert einen wichtigen Grund dafür: In den Katalysezyklen kann aus Acylmetallkomplexen Kohlenmonoxidgas, aus Carboxylatkomplexen gasförmiges Kohlendioxid freigesetzt werden, wobei jeweils unterschiedliche metallorganische Spezies gebildet werden. So können Carbonsäuren zu Syntheseäquivalenten von Acyl‐, Aryl‐ oder Alkylhalogeniden sowie von metallorganischen Reagentien werden. Dieser Aufsatz gibt einen Überblick über interessante katalytische Transformationen von Carbonsäuren und einigen aus ihnen in situ zugänglichen Derivaten. Er soll dazu einladen, diese neuen Methoden zu ergänzen, weiter zu entwickeln und in der organischen Synthese einzusetzen.
Optimal literature search for systematic reviews in surgeryKäthe Gooßen, Solveig Tenckhoff, Pascal Probst et al.|Langenbeck s Archives of Surgery|2017 Catalytic C–H Carboxylation of Terminal Alkynes with Carbon DioxideWithin the past years, several catalyst systems have been discovered that promote the carboxylation of terminal alkynes with formation of propiolic acids. This reaction concept is particularly topical in that it involves the functionalization of a C–H bond and the incorporation of CO2 into an organic molecule without need for strong bases or aggressive organometallic reagents. The present article reviews the development of this new reaction type and critically compares the reaction and catalyst concepts disclosed in the literature.