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Regioselective diversification of 2,1-borazaronaphthalenes: unlocking isosteric space via C-H activation

Davies, G. H. M ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1021/acs.joc.7b01331
  3. Abstract:
  4. Methods for the regioselective C-H borylation and subsequent cross-coupling of the 2,1-borazaronaphthalene core are reported. Azaborines are dependent on B-N/C=C isosterism when employed in strategies for developing diverse heterocyclic scaffolds. Although 2,1-borazaronaphthalene is closely related to naphthalene in terms of structure, the argument is made that the former has electronic similarities to indole. Based on that premise, iridium-mediated C-H activation has enabled facile installation of a versatile, nucleophilic coupling handle at a previously inaccessible site of 2,1-borazaronaphthalenes. A variety of substituted 2,1-borazaronaphthalene cores can be successfully borylated and further cross-coupled in a facile manner to yield diverse C(8)-substituted 2,1-borazaronaphthalenes. © 2017 American Chemical Society
  5. Keywords:
  6. Activation analysis ; Chemical activation ; Naphthalene ; Scaffolds ; Borylation ; C-h activation ; Cross-coupled ; Cross-couplings ; Isosteric ; Regioselectivity ; 2,1 borazaronaphthalene derivative ; Heterocyclic compound ; Iridium ; Naphthalene derivative ; Unclassified drug ; Bromination ; Chemical modification ; Covalent bond ; Electrophilicity ; High temperature ; Hydrogen bond ; Nucleophilicity ; Process optimization ; Proton transport ; Suzuki reaction
  7. Source: Journal of Organic Chemistry ; Volume 82, Issue 15 , 2017 , Pages 8072-8084 ; 00223263 (ISSN)
  8. URL: https://pubs.acs.org/doi/10.1021/acs.joc.7b01331