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The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki-Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described. [ABSTRACT FROM AUTHOR]

Synthesis and characterization of the new air-stable pre-catalyst (DPEPhos)Ni(2-mesityl)Br (C1) is reported, along with the application of this pre-catalyst in the cross-coupling of secondary amines/azoles with activated (hetero)aryl chlorides to afford tertiary (hetero)anilines. The performance of C1 in these cross-couplings is competitive with some of the best and/or most widely employed nickel catalysts for such transformations. [ABSTRACT FROM AUTHOR]

The utility of RockPhos, Ad-BippyPhos, JosiPhos (CyPF- tBu), and Mor-DalPhos in palladium-catalyzed C-O cross-coupling reactions involving aliphatic alcohols and (hetero)aryl halides under analogous conditions was examined, both at room temperature and at elevated temperature (90 °C). In general, the RockPhos-based catalyst system proved superior, especially at room temperature, but catalysts based on the other ligands examined also proved effective across a range of C-O cross-couplings, in some cases providing better catalytic performance than RockPhos. New reactivity was established in terms of the scope of room temperature reactions. Proof-of-principle examples of such cross-couplings involving aryl mesylates were also demonstrated. [ABSTRACT FROM AUTHOR]