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

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 bro...

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Bibliographic Details
Main Authors: Si, Xiaojia (Author) , Zhang, Lumin (Author) , Wu, Zuozuo (Author) , Rudolph, Matthias (Author) , Asiri, Abdullah M. (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: July 17, 2020
In: Organic letters
Year: 2020, Volume: 22, Issue: 15, Pages: 5844-5849
ISSN:1523-7052
DOI:10.1021/acs.orglett.0c01924
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.0c01924
Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/acs.orglett.0c01924
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Author Notes:Xiaojia Si, Lumin Zhang, Zuozuo Wu, Matthias Rudolph, Abdullah M. Asiri, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Gesehen am 16.09.2020
Physical Description:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.0c01924

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