cs9b03715_si_001.cif (3.99 MB)
Nickel-Catalyzed C–N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design
dataset
posted on 2019-09-16, 12:34 authored by Ryan T. McGuire, Julia F. J. Paffile, Yuqiao Zhou, Mark StradiottoThe
Ni(II) precatalyst (C1) featuring the phosphonite
ancillary ligand Phen-DalPhos (L1) was employed in the
cross-coupling of (hetero)anilines with (hetero)aryl chlorides and
in the diarylation of ammonia with (hetero)aryl chlorides to afford
heteroatom-dense di(hetero)arylamines. The PAd2-DalPhos precatalyst C4 provided complementary reactivity in cross-couplings of
indoles with (hetero)aryl chlorides. Taken together, the demonstration
of room-temperature reactivity within each of the reaction classes
examined and the observation of useful chemoselectivity at low loading
(≤0.5 mol % Ni) and on gram-scale distinguishes C1 and C4 from other metal catalysts (i.e., copper, palladium,
nickel, or other) within the field of C–N cross-coupling chemistry.