Synergistic photoredox and copper catalysis by diode-like coordination polymer with twisted and polar copper–dye conjugation

Yusheng Shi, Tiexin Zhang, Xiao-Ming Jiang, Gang Xu, Cheng He and Chunying Duan ()
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Yusheng Shi: Dalian University of Technology
Tiexin Zhang: Dalian University of Technology
Xiao-Ming Jiang: Chinese Academy of Sciences
Gang Xu: Chinese Academy of Sciences
Cheng He: Dalian University of Technology
Chunying Duan: Dalian University of Technology

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Synergistic photoredox and copper catalysis confers new synthetic possibilities in the pharmaceutical field, but is seriously affected by the consumptive fluorescence quenching of Cu(II). By decorating bulky auxiliaries into a photoreductive triphenylamine-based ligand to twist the conjugation between the triphenylamine-based ligand and the polar Cu(II)–carboxylate node in the coordination polymer, we report a heterogeneous approach to directly confront this inherent problem. The twisted and polar Cu(II)–dye conjunction endows the coordination polymer with diode-like photoelectronic behaviours, which hampers the inter- and intramolecular photoinduced electron transfer from the triphenylamine-moiety to the Cu(II) site and permits reversed-directional ground-state electronic conductivity, rectifying the productive loop circuit for synergising photoredox and copper catalysis in pharmaceutically valuable decarboxylative C(sp3)–heteroatom couplings. The well-retained Cu(II) sites during photoirradiation exhibit unique inner-spheric modulation effects, which endow the couplings with adaptability to different types of nucleophiles and radical precursors under concise reaction conditions, and distinguish the multi-olefinic moieties of biointeresting steride derivatives in their late-stage trifluoromethylation-chloration difunctionalisation.

Date: 2020
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DOI: 10.1038/s41467-020-19172-3

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