Sodium Butylated Hydroxytoluene: A Functional Group Tolerant, Eco-Friendly Base for Solvent-Free, Pd-Catalysed Amination
NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing
Semeniuchenko, Volodymyr,Braje, Wilfried M.,Organ, Michael G.
supporting information
p. 12535 - 12539
(2021/08/03)
Selective Monoarylation of Primary Anilines Catalyzed by Pd(dippf) and its Application in OLED Component Synthesis
Palladium 1,1′-bis(diisopropylphosphino)-ferrocene [Pd(dippf)] complexes were found to promote the monoarylation of primary anilines with unprecedented selectivities. They also allow the sequential arylation of primary anilines with two different aryl bromides in one pot. The reactions can be performed at low catalyst loadings (0.2 mol%) and high substrate concentrations. The synthetic utility of the optimum catalyst was demonstrated by the synthesis of various di- and triarylamines. A particular focus was set on compounds with carbazole and fluorene moieties as employed in state-of-the-art small-molecule organic light emitting diodes (OLEDs). (Figure presented.).
Grünberg, Matthias F.,Jia, Fan,Rivas-Nass, Andreas,Goo?en, Lukas J.
supporting information
p. 1589 - 1594
(2016/10/13)
Stable nickel(0) phosphites as catalysts for C-N cross-coupling reactions
Herein we describe the design and preparation of inexpensive, air-stable nickel phosphite-based catalysts for use in the C-N cross-coupling reaction. The combination of nickel tetrakis(triphenyl phosphite) {Ni[P(OPh) 3]4} and 1,1'-bis(diphenylphosphino)ferrocene (dppf), and in particular a newly developed catalyst (dppf)Ni[P(OPh)3] 2, were found to be extremely effective in catalyzing a range of amination reactions of anilines and amines with aryl chlorides. This new catalyst system offers an alternative to the bis(cyclooctadienyl)nickel [Ni(COD)2] and palladium(0) catalysts commonly used for C-N bond formation.
Kampmann, Sven S.,Sobolev, Alexandre N.,Koutsantonis, George A.,Stewart, Scott G.
supporting information
p. 1967 - 1973
(2014/07/07)
Synthesis and properties of phenylogous amides
Vinylogy is a widely accepted principle involving the transfer of electronic chemical character through a double bond, and many reactions have been developed by applying this concept. In contrast, phenylogy, which involves the connection of two substituen
Aminations of aryl bromides in water at room temperature
Unsymmetrical di- and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium.
Lipshutz, Bruce H.,Chung, David W.,Rich, Brian
supporting information; experimental part
p. 1717 - 1721
(2011/03/20)
Rapid and efficient microwave-assisted synthesis of aryl aminobenzophenones using Pd-catalyzed amination
Substituted aryl aminobenzophenone p38 MAP kinase inhibitors were synthesized in good to excellent yields using palladium-catalyzed aryl amination under conditions of microwave irradiation. Various ligands have been screened, and the reaction conditions w
Jensen, Thomas A.,Liang, Xifu,Tanner, David,Skjaerbaek, Niels
p. 4936 - 4947
(2007/10/03)
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