Dye-incorporated coordination polymers for direct photocatalytic trifluoromethylation of aromatics at metabolically susceptible positions

Tiexin Zhang, Xiangyang Guo, Yusheng Shi, Cheng He and Chunying Duan ()
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Tiexin Zhang: Dalian University of Technology
Xiangyang Guo: Dalian University of Technology
Yusheng Shi: Dalian University of Technology
Cheng He: Dalian University of Technology
Chunying Duan: Dalian University of Technology

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Direct trifluoromethylation of unactivated aromatic rings at metabolically susceptible positions is highly desirable in pharmaceutical applications. By incorporating thiophenes into the backbone of triphenylamine to enlarge its π-system, a new approach for constructing coordination polymers is reported for direct trifluoromethylation without prefunctionalization of the aryl precursors. The improved light-harvesting ability and well-modulated excited state redox potential of the designed polymers endow the generated CF3 radicals with suitable reactivity and enhance radical adduct oxidation in pores. The well-configurated interactions between the organic ligands distort the coordination geometry to create active interaction sites within the coordination polymer; thus, the substrates could be docked near the photoredox-active centres. The synergistic electronic and spatial effects in the confined pores balance the contradictory demands of electronic effects and reaction dynamics, achieving regio- and diastereoselective discrimination among reaction sites with unremarkable electronic/steric differences.

Date: 2018
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DOI: 10.1038/s41467-018-05919-6

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