DOI: 10.1021/acs.orglett.6c03891 ISSN: 1523-7060
Decatungstate-Photocatalyzed Tandem C–H/O–H Bond Addition-Cyclization of Alcohols with Olefins
Teng Zhang, Junqiao Wang, Lingfeng Wu, Cong-Qiao Xu, Ying Tan, Jun Li, Cheuk-Wai SoAbstract
Simultaneous activation of α-C(sp3)–H and O–H bonds in alcohols remains challenging because of their high bond dissociation energies. Here, we report an efficient strategy for tandem C–H/O–H bond addition of renewable alcohols to electrophilic olefins using inexpensive decatungstate photocatalysis under ambient conditions, affording diverse 1-oxo-2-amino-3-carbonitrile products (55 examples). Mechanistic and theoretical studies reveal that photoexcited [W10O32]4– mediates α-C(sp3)–H activation and subsequent cyclization, establishing a versatile photocatalytic platform for simultaneous C–H and O–H functionalization.