10.1021/acscatal.9b03715.s001
Ryan T. McGuire
Ryan T.
McGuire
Julia F. J. Paffile
Julia F. J.
Paffile
Yuqiao Zhou
Yuqiao
Zhou
Mark Stradiotto
Mark
Stradiotto
Nickel-Catalyzed C–N Cross-Coupling of Ammonia,
(Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides
Enabled by Ligand Design
American Chemical Society
2019
Hetero
Ni
hetero
reactivity
C 1
chloride
cross-coupling
PAd 2-DalPhos precatalyst C 4
2019-09-16 12:34:28
Dataset
https://acs.figshare.com/articles/dataset/Nickel-Catalyzed_C_N_Cross-Coupling_of_Ammonia_Hetero_anilines_and_Indoles_with_Activated_Hetero_aryl_Chlorides_Enabled_by_Ligand_Design/9850937
The
Ni(II) precatalyst (<b>C1</b>) featuring the phosphonite
ancillary ligand Phen-DalPhos (<b>L1</b>) 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 <b>C4</b> 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 <b>C1</b> and <b>C4</b> from other metal catalysts (i.e., copper, palladium,
nickel, or other) within the field of C–N cross-coupling chemistry.