Products Cited in Publications Worldwide Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling

Computational Methods Enable the Prediction of Improved Catalysts for Nickel-Catalyzed Cross-Electrophile Coupling

Michelle E. Akana; Sergei Tcyrulnikov; Brett D. Akana-Schneider; Giselle P. Reyes; Sebastien Monfette; Matthew S. Sigman; Eric C. Hansen; Daniel J. Weix

DOI:

Abstract

Cross-electrophile has emerged as an attractive and efficient method for the synthesis of C(sp2)–C(sp3) bonds. These reactions are most often catalyzed by complexes of nitrogenous ligands, especially 2,2′-bipyridines. Precise prediction, selection, and design of optimal ligands remains challenging, despite significant increases in reaction scope and mechanistic understanding. Molecular parameterization and statistical modeling provide a path to the development of improved ligands that will enhance the selectivity of existing reactions and broaden the scope of electrophiles that can be coupled. Herein, we describe the generation of a computational ligand library, correlation of observed reaction outcomes with features of the ligands, and the in silico design of improved ligands for Ni-catalyzed cross-electrophile . The new nitrogen-substituted ligands display a 5-fold increase in selectivity for product formation versus homodimerization when compared to the current state of the art. This increase in selectivity and yield was general for several cross-electrophile couplings, including the challenging of an aryl chloride with an N-alkylpyridinium salt.

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A127831385698-56-298%

4,4' -Bis(N,N-dimethylamino)-2,2' -bipyridine

30.0/250mg

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