An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions

• Published in: European journal of organic chemistry Vol. 2015; no. 27; pp. 5995 - 6004
• Main Authors: Kampmann, Sven S., Skelton, Brian W., Wild, Duncan A., Koutsantonis, George A., Stewart, Scott G.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Amines; C-N bond formation; Chemistry; Chemistry, Organic; Cross-coupling; Homogeneous catalysis; Nickel; Physical Sciences; Science & Technology; HALIDES; PALLADIUM; C-N bond formation; Amines; COMPLEXES; BOND FORMATION; REDUCTIVE ELIMINATION; Cross-coupling; LIGANDS; Homogeneous catalysis; PD-CATALYZED AMINATION; NITROGEN; Nickel; ARYL CHLORIDES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201500734

In this report we describe the design and preparation of a new air‐stable nickel phosphite based catalyst for unique C–N bond forming processes. Specifically, (BINAP)Ni[P(OPh)3]2, is presented as an effective catalyst for a range of amination reactions between aryl halides and primary alkylamines. The results are supported by relevant kinetic studies, DFT calculations and a catalytic cycle indicating possible reaction intermediates. The amination reaction between a series of aryl halides and primary alkylamines is described using a new air‐stable nickel phosphite based catalyst (BINAP)Ni[P(OPh)3]2.