Visible Light-Induced α-C(sp3)–H Acetalization of Saturated Heterocycles Catalyzed by a Dimeric Gold Complex

• DOI: 10.1021/acs.orglett.0c01924
• Publication Date: 2020-07-17T20:24:10Z
• Authors: Xiaojia Si; Lumin Zhang; Zuozuo Wu; Matthias Rudolph; Abdullah M. Asiri; A. Stephen K. Hashmi
• Keywords: 01 natural sciences; 0104 chemical sciences

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.