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Palladium-Catalyzed Direct

Molecules (Basel, Switzerland), 2023-05, Vol.28 (9) [Peer Reviewed Journal]

COPYRIGHT 2023 MDPI AG ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules28093977

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  • Title:
    Palladium-Catalyzed Direct
  • Author: Chmovzh, Timofey N ; Kudryashev, Timofey A ; Alekhina, Daria A ; Rakitin, Oleg A
  • Subjects: Palladium
  • Is Part Of: Molecules (Basel, Switzerland), 2023-05, Vol.28 (9)
  • Description: Palladium-catalyzed direct (het)arylation reactions of strongly electron-withdrawing tricyclic benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative were studied; the conditions for the selective formation of mono- and bis-aryl derivatives were found. The reaction of 4,8-dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) with thiophenes in the presence of palladium acetate as a catalyst and potassium pivalate as a base, depending on the conditions used, selectively gave both mono- and bis-thienylated benzo-bis-thiadiazoles in low to moderate yields; arenes were found to be inactive in these reactions. It was discovered that direct C–H arylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with bromo(iodo)arenes and -thiophenes in the presence of Pd(OAc)2 and di-tert-butyl(methyl)phosphonium tetrafluoroborate salt is a powerful tool for the selective formation of 4-mono- and 4,8-di(het)arylated benzo-bis-thiadiazoles. Oxidative double C–H hetarylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with thiophenes in the presence of Pd(OAc)[sub.2] and silver (I) oxide in DMSO was successfully employed to prepare bis-thienylbenzo-bis-thiadiazoles in moderate yields.
  • Publisher: MDPI AG
  • Language: English
  • Identifier: ISSN: 1420-3049
    EISSN: 1420-3049
    DOI: 10.3390/molecules28093977
  • Source: PubMed Central (Open access)
    Geneva Foundation Free Medical Journals at publisher websites
    Directory of Open Access Journals
    Alma/SFX Local Collection
    ProQuest Central
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