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      Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp 2)–H Functionalization

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      Publication date (Electronic):
      Journal: Organic Letters
      Publisher: American Chemical Society

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          Abstract

          The palladium-catalyzed C(sp 2)–H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described. This method allows for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were readily demonstrated, illustrating the synthetic utility of the obtained benzocyclobutenone-derived nitrones for the construction of polycyclic nitrogen-containing scaffolds.

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          Beyond Directing Groups: Transition-Metal-Catalyzed CH Activation of Simple Arenes

          Nadine Kuhl, Matthew Hopkinson, Joanna Wencel-Delord … (2012)
          Article 0 comments Cited 312 times – based on 0 reviews     Review now
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            Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups

            Zhanxiang Liu, Yuhong Zhang, Zhengkai Chen … (2015)
            In this review, a summary of transition metal-catalyzed C–H activation by utilizing the functionalities as directing groups is presented. Transition metal-catalyzed direct functionalization of C–H bonds is one of the key emerging strategies that is currently attracting tremendous attention with the aim to provide alternative environmentally friendly and efficient ways for the construction of C–C and C–hetero bonds. In particular, the strategy involving regioselective C–H activation assisted by various functional groups shows high potential, and significant achievements have been made in both the development of novel reactions and the mechanistic study. In this review, we attempt to give an overview of the development of utilizing the functionalities as directing groups. The discussion is directed towards the use of different functional groups as directing groups for the construction of C–C and C–hetero bonds via C–H activation using various transition metal catalysts. The synthetic applications and mechanistic features of these transformations will be discussed, and the review is organized on the basis of the type of directing groups and the type of bond being formed or the catalyst.
            Article 0 comments Cited 180 times – based on 0 reviews     Review now
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              Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes.

              Gabriele Fumagalli, Steven Stanton, John Bower (2017)
              In this review, synthetic and mechanistic aspects of key methodologies that exploit C-C single-bond cleavage of strained ring systems are highlighted. The focus is on transition-metal-catalyzed processes that are triggered by C-C bond activation and β-carbon elimination, with the review concentrating on developments from mid-2009 to mid-2016.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Org Lett
                Journal ID (iso-abbrev): Org Lett
                Journal ID (publisher-id): ol
                Journal ID (coden): orlef7
                Title: Organic Letters
                Publisher: American Chemical Society
                ISSN (Print): 1523-7060
                ISSN (Electronic): 1523-7052
                Publication date (Electronic): 25 May 2022
                Publication date (Print): 10 June 2022
                Volume: 24
                Issue: 22
                Pages: 3960-3964
                Affiliations
                Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland
                Author notes
                Author information
                https://orcid.org/0000-0002-0823-4675
                Article
                DOI: 10.1021/acs.orglett.2c01317
                PMC ID: 9278523
                PubMed ID: 35613705
                SO-VID: 25bfd76c-4e77-4d03-93f1-a8a47cf9facd
                Copyright © © 2022 The Authors. Published by American Chemical Society
                License:

                Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained ( https://creativecommons.org/licenses/by/4.0/).

                History
                Funding
                Funded by: Narodowe Centrum Nauki, doi 10.13039/501100004281;
                Award ID: UMO-2017/26/E/ST5/00388
                Funded by: Ministerstwo Edukacji i Nauki, doi 10.13039/501100004569;
                Award ID: 0235/DIA/2019/48
                Funded by: Narodowe Centrum Nauki, doi 10.13039/501100004281;
                Award ID: UMO-2020/37/N/ST4/00777
                Categories
                Subject: Letter
                Custom metadata
                document-id-old-9 ol2c01317
                document-id-new-14 ol2c01317
                ccc-price

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry

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