Journal
ACS CATALYSIS
Volume 11, Issue 6, Pages 3507-3515Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c00209
Keywords
porous polymers; macroligand; nickel complex; cross-coupling; heterobiaryl; C-H arylation; LiHMDS
Categories
Funding
- European Union [720996]
- Deutsche Forschungsgemeinschaft (DFG) [WI 4721/3-1]
- CNRS through Momentum 2018 excellence grant
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The study demonstrates the successful development of a heterogeneous nickel catalyst using a porous organic polymer as a macroligand, which can be applied to various arylation reactions with good recyclability.
Direct C-H functionalization catalyzed by a robust and recyclable heterogeneous catalyst is highly desirable for sustainable fine chemical synthesis. Bipyridine units covalently incorporated into the backbone of a porous organic polymer were used as a porous macroligand for the heterogenization of a molecular nickel catalyst. A controlled nickel loading within the porous macroligand is achieved, and the nickel coordination to the bipyridine (bpy) sites is assessed at the molecular level using IR and solid-state NMR spectroscopy. The heterogenized Ni-bpy catalyst was successfully applied to the direct and fully selective C2 arylation of benzothiophenes, thiophene, and selenophene, as well as for the arylation of free NH-indole. Recyclability of the catalyst was achieved by employing hydride activators to reach a cumulative turnover number of more than 300 after seven cycles of catalysis, which corresponds to a total productivity of 12 g of 2-phenylbenzothiophene, chosen as model target biaryl, per gram of catalyst.
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