For Publishers
DiscoveryMetadataPeer reviewHostingPublishing
For Researchers
JoinPublishReviewCollect
Register
Blog
About
Search
Advanced search
My ScienceOpen
Search
For Publishers
For Researchers
Blog
About
0
views
42
references
 Top references
cited by
0
    
0 reviews
 Review
0
comments
 Comment
0
recommends
+1 Recommend
0 collections
    0
    shares
      160
      similar
       All similar
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Photoinduced Intermolecular Radical Hydroalkylation of Olefins via Ligated Boryl Radicals-Mediated Halogen Atom Transfer

      rapid-communication

      Read this article at

      ScienceOpenPublisherPMC
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Light-mediated Halogen-Atom Transfer (XAT) has become a significant methodology in contemporary synthesis. Unlike α-aminoalkyl and silyl radicals, ligated boryl radicals (LBRs) have not been extensively explored as halogen atom abstractors. In this study, we introduce NHC-ligated boranes as optimal radical chain carriers for the intermolecular reductive radical hydroalkylation and hydroarylation of electron-deficient olefins by using direct UV-A light irradiation. DFT analysis allowed us to rationalize the critical role of the NHC ligand in facilitating efficient chain propagation.

          Related collections

          Most cited references42

          • Record: found
          • Abstract: found
          • Article: found
          Is Open Access

          Characterizing chain processes in visible light photoredox catalysis † †Electronic supplementary information (ESI) available: Quantum yield measurements, luminescence quenching experiments, “light/dark” experiments, and time course data. See DOI: 10.1039/c5sc02185e

          Megan A Cismesia, Tehshik Yoon (2015)
          The combination of quantum yield and luminescence quenching measurements provides a method to rapidly characterize the occurrence of chain processes in a variety of photoredox reactions.
          Article 0 comments Cited 223 times – based on 0 reviews     Review now
            Bookmark
            • Record: found
            • Abstract: found
            • Article: not found

            Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.

            Patricia Zhang, Chi Le, David MacMillan (2016)
            A strategy for cross-electrophile coupling has been developed via the merger of photoredox and transition metal catalysis. In this report, we demonstrate the use of commercially available tris(trimethylsilyl)silane with metallaphotoredox catalysis to efficiently couple alkyl bromides with aryl or heteroaryl bromides in excellent yields. We hypothesize that a photocatalytically generated silyl radical species can perform halogen-atom abstraction to activate alkyl halides as nucleophilic cross-coupling partners. This protocol allows the use of mild yet robust conditions to construct Csp(3)-Csp(2) bonds generically via a unique cross-coupling pathway.
            Article 0 comments Cited 142 times – based on 0 reviews     Review now
              Bookmark
              • Record: found
              • Abstract: not found
              • Article: not found

              Formation of CC Bonds by Addition of Free Radicals to Alkenes

              Bernd Giese (1983)
              Article 0 comments Cited 106 times – based on 0 reviews     Review now
                Bookmark
                All references

                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): 01 July 2024
                Publication date Collection: 12 July 2024
                Volume: 26
                Issue: 27
                Pages: 5839-5843
                Affiliations
                [† ]Flow Chemistry Group, van’t Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam , 1098 XH Amsterdam, The Netherlands
                [‡ ]The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine , Shanghai 201203, China
                [§ ]PhotoGreen Lab, Department of Chemistry, University of Pavia , 27100 Pavia, Italy
                [∥ ]SynCat Lab, Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma , 43124 Parma, Italy
                Author notes
                Author information
                https://orcid.org/0000-0003-2201-4828
                https://orcid.org/0000-0001-7114-267X
                Article
                DOI: 10.1021/acs.orglett.4c02034
                PMC ID: 11250028
                PubMed ID: 38950385
                SO-VID: 6d751934-d0cd-4d08-989b-e1ee6f82e7b5
                Copyright © © 2024 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
                Date received : 03 June 2024
                Date accepted : 26 June 2024
                Date revision received : 21 June 2024
                Funding
                Funded by: Narodowe Centrum Nauki, doi 10.13039/501100004281;
                Award ID: 2019/32/T/ST4/00426
                Funded by: Ministero dell''Università e della Ricerca, doi 10.13039/501100021856;
                Award ID: NA
                Funded by: China Scholarship Council, doi 10.13039/501100004543;
                Award ID: NA
                Categories
                Subject: Letter
                Custom metadata
                document-id-old-9 ol4c02034
                document-id-new-14 ol4c02034
                ccc-price

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

                Comments

                Comment on this article