Abstract
The design, synthesis, commercialization and application of air-stable Ni(II)/Josiphos complexes has been realized in a collaboration between Solvias and ICBMS (University Lyon 1). The Ni-complexes are utilized as versatile precatalysts for diverse cross-coupling reactions. Apart from being active in established C-C and C-N couplings at low catalyst loadings, the novel Ni-precatalysts enabled the development of the challenging monoarylation of ammonia, ammonia surrogates and even alkylammonium chlorides with aryl carbamates. Finally, the α-arylation of acetone with aryl chlorides, carbamates and pivalates was demonstrated using the Ni(II)/Josiphos precatalysts.
Highlights
Since more than two decades, the Ligands & SpecialtyProducts unit at Solvias provides full service in the field of homogeneous and heterogeneous metal catalysis
The combination of a broad ligand and catalyst portfolio with capabilities in the development of chemocatalyzed reactions supported by a high-throughput experimentation (HTE) platform allows for the investigation of a wide variety of different transformations such as homogeneous and heterogeneous hydrogenations, C–C and C–X couplings, carbonylations, aminations and recently
We launched a research program to investigate the synthesis as well as the application of air stable Ni(ii)/Josiphos precatalysts, of which several have been commercialized. These precatalysts allowed to achieve the challenging arylation of primary building blocks such as ammonia and acetone
Summary
Products unit at Solvias provides full service in the field of homogeneous and heterogeneous metal catalysis. A main drawback in Ni-chemistry is the high air and moisture sensitivity of Ni(0) precatalysts such as Ni(COD) In this context, we launched a research program to investigate the synthesis as well as the application of air stable Ni(ii)/Josiphos precatalysts, of which several have been commercialized. Its electron-withdrawing character facilitates the reductive elimination to set free the desired reactive L-Ni(0) species while at the same time forming benzonitrile derivatives in catalytic amounts in the reaction media These latter species could further enhance the stability of Ni(0) intermediate by forming Ni(η2-NC-Ar) complexes as demonstrated earlier by the Hartwig group.[5] The same synthetic protocol can be extended to other Josiphos ligands enabling the formation of a plethora of air-stable, but in reaction media highly active, Ni(ii)-precatalysts.
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