1449248-80-9Relevant academic research and scientific papers
Palladium C-N bond formation catalysed by air-stable robust polydentate ferrocenylphosphines: A comparative study for the efficient and selective coupling of aniline derivatives to dichloroarene
Platon, Melanie,Roger, Julien,Royer, Sylviane,Hierso, Jean-Cyrille
, p. 2072 - 2080 (2014/06/24)
The arylation of aniline derivatives with dichloroarenes under a low palladium content (below the currently used 5 to 10 mol%) was studied using nine different ferrocenylphosphine ligands, including the easily accessible 1,1′-bis(diphenylphosphino)ferrocene, DPPF. The electron-enriched air-stable tridentate ferrocenylpolyphosphine 1,2-bis(diphenylphosphino)- 1′-(diisopropylphosphino)-4-tert-butylferrocene, L5, employed in 2 mol% in combination with 1 mol% [PdCl(η3-C3H 5)]2 allows an efficient and selective coupling, while such demanding substrates currently induce chloroarene homocoupling and/or dehalogenation processes. The scope and limitation of the optimized system are explored, with a focus on electron-poor fluoroanilines (deactivated nucleophiles) and electron-rich methylated and methoxylated dichlorobenzenes (deactivated electrophiles). The Royal Society of Chemistry 2014.
Metal-free synthesis of secondary arylamines: An aliphatic-to-aromatic transformation
Barros, M. Teresa,Dey, Suvendu S.,Maycock, Christopher D.
supporting information, p. 742 - 747 (2013/03/13)
An efficient method for the N-arylation of primary and some secondary amines using 2-halocyclohex-2-enones in an aliphatic-to-aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2-halocyclohex-2-enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal-free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications. Copyright
