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  • PAd2-DalPhos Enables the Nickel-Catalyzed C-N Cross-Coupling of Primary Heteroarylamines and (Hetero)aryl Chlorides.

PAd2-DalPhos Enables the Nickel-Catalyzed C-N Cross-Coupling of Primary Heteroarylamines and (Hetero)aryl Chlorides.

Angewandte Chemie (International ed. in English) (2019-03-16)
Jillian S K Clark, Michael J Ferguson, Robert McDonald, Mark Stradiotto
ABSTRACT

Base-metal catalysts capable of enabling the assembly of heteroatom-dense molecules by cross-coupling of primary heteroarylamines and (hetero)aryl chlorides, while sought-after given the ubiquity of unsymmetrical di(hetero)arylamino fragments in pharmacophores, are unknown. Herein, we disclose the new "double cage" bisphosphine PAd2-DalPhos (L2). The derived air-stable NiII pre-catalyst C2 functions well at low loadings in challenging test C-N cross-couplings with established substrates, and facilitates the first Ni-catalyzed C-N cross-couplings of primary five- or six-membered ring heteroarylamines and activated (hetero)aryl chlorides, with synthetically useful scope that is competitive with Pd catalysis.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
PAd2-DalPhos, ≥95%
Sigma-Aldrich
PAd2-DalPhos Ni(o-tolyl)Cl