7463-28-7Relevant articles and documents
Increasing the Activity of Copper Guanidine Quinoline Catalysts: Substitution at the Quinoline Backbone Leads to Highly Active Complexes for ATRP
Kr?ckert, Konstantin W.,Mannsperger, Johannes S.,R?sener, Thomas,Hoffmann, Alexander,Herres-Pawlis, Sonja
supporting information, p. 832 - 842 (2021/03/31)
Copper bromide complexes with the ligands TMG6NO2qu, TMG6Brqu, TMG6Methoxyqu, TMG6NMe2qu, TMG6EHOqu and TMG6dBAqu were examined regarding their activity in atom transfer radical polymerization (ATRP). The ligands were inspired by 1,1,3,3-tetramethyl-2-(quinolin-8-yl)guanidine (TMGqu) and the substituents have been chosen with a large range between electron withdrawing and donating abilities. The donor properties of the ligands can be strongly influenced and further highly active catalysts based on these systems can be obtained. The ligands with strong donating moieties were in addition modified by alkyl groups to increase the solubility in apolar monomers like styrene. CuI and CuII bromide complexes were crystallised and the structural data correlated to the different substituents and the catalyst activity. The electrochemical potentials E1/2, the equilibrium constants KATRP and rate constants kact and kdeact were determined. Polymerizations of styrene were conducted in solution whereas the catalyst based on TMG6EHOqu shows a good solubility and performance in bulk.
Visible-light-induced Beckmann rearrangement by organic photoredox catalysis
Tang, Li,Wang, Zhi-Lv,Wan, Hai-Lan,He, Yan-Hong,Guan, Zhi
supporting information, p. 6182 - 6186 (2020/09/01)
A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.
A one pot protocol to convert nitro-arenes into: N-aryl amides
Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
, p. 4040 - 4044 (2020/02/04)
A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.