PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines.

PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines.
Angew Chem Int Ed Engl. 2019 Jan 03;:
Authors: Tassone J, England E, MacQueen P, Ferguson M, Stradiotto M
Abstract
The base metal-catalyzed C-N cross-coupling of bulky alpha,alpha,alpha-trisubstituted primary alkylamines with (hetero)aryl electrophiles represents a challenging and under-developed class of transformations that is of significant potential utility, including in the synthesis of lipophilic active pharmaceutical ingredients. Herein, we report that a new, air-stable Ni(II) pre-catalyst incorporating the optimized ancillary ligand PhPAd-DalPhos enables such transformations of (hetero)aryl chloride, bromide, and tosylate electrophiles to be carried out for the first time with substrate scope rivalling that achieved using state-of-the-art Pd catalysts, including room temperature cross-couplings of (hetero)aryl chlorides that are unprecedented for any catalyst (Pd, Ni, or other).
PMID: 30605255 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 3, 2019 Category: Chemistry Authors: Tassone J, England E, MacQueen P, Ferguson M, Stradiotto M Tags: Angew Chem Int Ed Engl Source Type: research