145567-64-2Relevant articles and documents
Direct access to: N -alkylated amines and imines via acceptorless dehydrogenative coupling catalyzed by a cobalt(ii)-NNN pincer complex
Midya, Siba P.,Pitchaimani, Jayaraman,Landge, Vinod G.,Madhu, Vedichi,Balaraman, Ekambaram
, p. 3469 - 3473 (2018/07/29)
A simple, phosphine-free Co(ii)-NNN pincer complex catalyzed direct N-alkylation of anilines with alcohols via hydrogen auto-transfer (HA) and selective acceptorless dehydrogenative coupling (ADC) of benzylamines with alcohols affording imines with the liberation of molecular hydrogen and water is reported.
An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions
Kampmann, Sven S.,Skelton, Brian W.,Wild, Duncan A.,Koutsantonis, George A.,Stewart, Scott G.
supporting information, p. 5995 - 6004 (2015/09/22)
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.
Nickel-on-charcoal-catalyzed aromatic aminations and Kumada couplings: Mechanistic and synthetic aspects
Tasler, Stefan,Lipshutz, Bruce H.
, p. 1190 - 1199 (2007/10/03)
Protocols for aromatic aminations and Kumada couplings catalyzed by 'heterogeneous' nickel-on-charcoal (Ni/C) have been revised, making them simpler and more time efficient. For both types of reactions, reduction of the catalyst precursor Ni(II)/C using n-BuLi prior to addition of a substrate can be avoided. Instead, in amination reactions, the amine in combination with lithium tert-butoxide was found to convert Ni(II)/C to active Ni(0). For Kumada couplings, direct reduction of Ni(II)/C by the Grignard reagent is easily achieved. Reactions run in the presence of triarylphosphine ligands of varying substitution patterns and with differing electronic properties provided insight into the mechanism of these nickel-catalyzed transformations. Ligandless Kumada couplings were facile with aryl Grignards, which may be a consequence of π-complexation of nickel by the aryl group in the reagent. Larger scale reactions of both types of couplings have been successfully performed, suggesting that Ni/C-based processes can be scaled-up as needed.
