267428-18-2

Upstream product

• 107-10-8 propylamine 
• 50-00-0 formaldehyd 
• 96-76-4 2,4-di-tert-Butylphenol 

Relevant academic research and scientific papers

Accelerated syntheses of amine-bis(phenol) ligands in polyethylene glycol or "on water" under microwave irradiation

Pure amine-bis(phenol) ligands are readily accessible in high yield, often >90%, when the Mannich condensation reactions are performed "on water" or in poly(ethyleneglycol) (PEG). Microwave-assisted synthesis dramatically reduces the time and energy required to prepare these molecules, typically from 24 h to 5 min. The approach seems to be widely applicable (7 amines and 5 phenols were tested to yield a diverse set of bis(phenol) ligands). Significant improvements in yield were observed for ligands derived from di-tert-amyl and di-tert-butyl phenols, possibly resulting from a hydrophobic effect. Single crystal X-ray diffraction data for the ligand derived from p-cresol and N,N-dimethylethylenediamine is reported.

Synthesis and structure of amine-bridged bis(phenolate) lanthanide complexes and their application in the polymerization of ε-caprolactone

A series of lanthanide complexes 1-8 were afforded by the amine elimination reactions of amine-bridged bis(phenols) H2L1-3 [L 1-3 = Et2NCH2CH2N{CH 2-(2-O-C6H2-R2-3-R 1-5)2, R1 = tBu, R2 = tBu (L1); R1 = Me, R2 = tBu (L2); R1 = Me, R2 = Me (L 3)] and H2L4-6 [L4-6 = CH 3CH2CH2N{CH2-(2-O-C 6H2-R2-3-R1-5)}2, R 1 = tBu, R2 = tBu (L4); R1 = Me, R2 = tBu (L5); R 1 = Me, R2 = Me (L6)] with Ln[N(SiMe 3)2]3 (Ln = La, Gd). The bis(phenolate) lanthanide amides L1-6La[N(SiMe3)2] (1-6) were given by the reactions of La[N(SiMe3)2]3 with H2L1-6 in 1:1 M ration in THF. The bis(phenolate) lanthanide complexes Ln2[L6]3 (Ln = La (7), Ln = Gd (8)) were given by the reactions of Ln[N(SiMe3) 2]3(Ln = La, Ga) with H2L6 in 2:3 M ratio in THF. Complexes 3 and 8 have been characterized by X-ray crystal structural analysis. The structure of complexes 3 reveals that it has unsolvated centrosymmetric dimer, built around a central, planar La2O 2 ring. Complex 8 possesses a THF-solvated unsymmetric dimer. The coordination geometry in complexes 3 and 8 around each of the lanthanide metal atoms can be described as a distorted octahedron. The catalytic properties of complexes 1-6 on the ring-opening polymerization of ε-caprolactone have been studied. The results show that lanthanide amides complexes 1-6 are efficient catalysts for the ring-opening polymerization of ε-caprolactone.

IRON BISPHENOLATE COMPLEXES AND METHODS OF USE AND SYNTHESIS THEREOF

The present application, relates to iron bisphenolate complexes and methods of use and synthesis thereof. The iron complexes are prepared from tridentate or tetradentate ligands of Formula I: wherein R1 and R2 are as defined herein. Also provided are methods and processes of using the iron bisphenolate complexes as catalysts in cross-coupling reactions and in controlled radical polymerizations.

Catalytic alkylation of aryl Grignard reagents by iron(iii) amine-bis(phenolate) complexes

Reaction of n-propylamino-N,N-bis(2-methylene-4-tert-butyl-6-methylphenol), H2L1, n-propylamino-N,N-bis(2-methylene-4,6-di-tert-butylphenol), H2L2, and benzylamino-N,N-bis(2-methylene-4-tert-butyl-6- methylphenol), H2L3, with anhydrous ferric chloride in the presence of base yields the products, [FeL1(μ-Cl)]2 (1), [FeL2(μ-Cl)]2 (2) and [FeL3(μ-Cl)]2 (3). In the solid state, these complexes exist as chloride-bridged dimers giving distorted trigonal bipyramidal iron(iii) ions. Reaction of H2L1 with FeBr 3, however, results in the formation of a tetrahedral iron(iii) complex possessing two bromide ligands. The amine-bis(phenolate) ligand is bidentate in this complex and bonds to the iron(iii) ion via the phenolate O-donors. The central amine donor is protonated, resulting in a quaternized ammonium fragment and the iron(iii) centre possesses a negative formal charge. As a result, this complex is zwitterionic and formulated as FeBr2L1H (4). Complex 1 is an air-stable, non-hygroscopic, single-component catalyst for C-C cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides, including chlorides. Good to excellent yields of cross-coupled products are obtained in diethyl ether at room temperature. In some cases where low yields are obtained under these conditions, the use of microwave-assisted heating of the reaction mixture can improve yields. The Royal Society of Chemistry 2011.