Construction of β-Heteroarylated Aliphatic Aldehydes via Pd-Catalyzed and Ag-Mediated Redox-Relay Oxidative Heck Reactions

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Herein, we report the first example of Pd-catalyzed and Ag-mediated redox-relay oxidative Heck reactions of furans/thiophenes with cis-alkenols to construct β-heteroarylated aliphatic aldehydes. Parallel kinetic isotope effect (KIE) experiments reveal that C-H bond breaking of the heterocycle might be involved in the rate-determining step. This approach features a broad substrate scope while enabling straightforward access to fluoroboron fluorescent and anti-Kasha dual-emission fluorescent materials. The novel fluorescent materials can selectively accumulate in lysosomes. In addition, the nanoparticles of the anti-Kasha dual-emission material can be used for two-channel emission-intensity-ratio imaging of HeLa cells, which favors observing the local cellular information and intercellular structures.

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