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      Palladium Catalysis: Dependence of the Efficiency of C–N Bond Formation on Carboxylate Ligand and Metal Carboxylate or Carboxylic Acid Additive

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      Publication date (Electronic):
      Journal: ACS Omega
      Publisher: American Chemical Society

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          Abstract

          The Pd-catalyzed inter- and intramolecular reactions of nitrogen compounds are often carried out with palladium carboxylates, sometimes in the presence of carboxylic acids or alkali metal carboxylates. This Mini-Review highlights the dependence of the reaction efficiency on the nature of the ligand and the carboxylate additives. The proposed reaction mechanisms are presented with, as far as possible, personal comments.

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          Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates.

          Serge Gorelsky, David LaPointe, Keith Fagnou (2008)
          The concerted metalation-deprotonation mechanism predicts relative reactivity and regioselectivity for a diverse set of arenes spanning the entire spectrum of known palladium-catalyzed direct arylation coupling partners. An analysis following an active strain model provides a more complete portrayal of the important arene/catalyst parameters leading to a successful coupling. The breadth of arenes whose reactivity can be predicted by the CMD mechanism indicates that it may be far more widespread than previously imagined.
          Article 0 comments Cited 135 times – based on 0 reviews     Review now
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            Catalytic intermolecular direct arylation of perfluorobenzenes.

            Marc Lafrance, Christopher N. Rowley, Tom. Woo … (2006)
            Penta-, tetra-, tri-, and difluorobenzenes undergo direct arylation with a wide range of arylhalides in high yield. Inverse reactivity is observed compared to the common electrophilic aromatic substitution pathway since electron-deficient, C-H acidic arenes react preferentially. Computational studies indicate that C-H bond cleavage occurs via a concerted carbon-palladium and carbon-hydrogen bond cleaving event involving a carbonate or a bromide ligand. The reactions are rapid, require only a slight excess of the perfluoroarene reagent, and utilize commercially available, air-stable catalyst precursors.
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              Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed CH Activation Using Dioxygen as the Oxidant

              Chun Li Zhang, Zhuangzhi Shi, Si Li … (2009)
              Article 0 comments Cited 93 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 08 March 2024
                Publication date Collection: 19 March 2024
                Volume: 9
                Issue: 11
                Pages: 12292-12306
                Affiliations
                [1]Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS, Université de Reims Champagne-Ardenne , B.P. 1039, 51687 Reims Cedex 2, France
                Author notes
                Author information
                https://orcid.org/0000-0002-1276-4206
                Article
                DOI: 10.1021/acsomega.4c00468
                PMC ID: 10955574
                PubMed ID: 38524407
                SO-VID: 30201693-670d-4814-b841-163b3e299a16
                Copyright © © 2024 The Author. Published by American Chemical Society
                License:

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 15 January 2024
                Date accepted : 20 February 2024
                Date revision received : 09 February 2024
                Categories
                Subject: Mini-Review
                Custom metadata
                document-id-old-9 ao4c00468
                document-id-new-14 ao4c00468
                ccc-price

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