Visible light-induced α-C(sp3)-H acetalization of saturated heterocycles catalyzed by a dimeric gold complex

• Verfasst von: Si, Xiaojia [VerfasserIn]
• Verfasst von: Zhang, Lumin [VerfasserIn]
• Verfasst von: Wu, Zuozuo [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Asiri, Abdullah M. [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Visible light-induced α-C(sp3)-H acetalization of saturated heterocycles catalyzed by a dimeric gold complex
• Verf.angabe: Xiaojia Si, Lumin Zhang, Zuozuo Wu, Matthias Rudolph, Abdullah M. Asiri, and A. Stephen K. Hashmi
• E-Jahr: 2020
• Jahr: July 17, 2020
• Umfang: 6 S.
• Fussnoten: Gesehen am 16.09.2020
• Titel Quelle: Enthalten in: Organic letters
• Ort Quelle: Washington, DC : ACS, 1999
• Jahr Quelle: 2020
• Band/Heft Quelle: 22(2020), 15, Seite 5844-5849
• ISSN Quelle: 1523-7052
• DOI: doi:10.1021/acs.orglett.0c01924
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1733105824

Abstract

Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)-H dehydrogenative cross-couplings of ethers, tetrahydrothiophenes, and pyrrolidines were achieved under visible light irradiation by using iodobenzene and an in situ-formed gold complex. The broad functional group compatibility and substrate scope indicate that our strategy is a promising way to synthesize acetal analogues. The method was successfully applied in late-stage modifications of bioactive molecules. Gram scale syntheses and mechanistic studies are also presented.