485394-21-6

Upstream product

• 209850-76-0 2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]aniline 
• 321848-64-0 (4S)-2-(2-bromophenyl)-4-phenyl-4,5-dihydro-1,3-oxazole 
• 32621-46-8 diphenylamine-2,2'-dicarbonyl chloride 
• 56613-80-0 D-2-phenylglycinol 
• 579-92-0 Vanadox 
• 118-48-9 isatoic anhydride 
• 815575-17-8 2,2'-bis[N-(1S)-(1-phenyl-2-hydroxyethyl)carbamoyl]diphenylamine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 485394-12-5 2-Amino-N-((S)-2-chloro-1-phenyl-ethyl)-benzamide 
• 209850-72-6 N-[(1S)-2-hydroxy-1-phenylethyl]-2-aminobenzamide 

Relevant academic research and scientific papers

Iron pincer complexes as catalysts and intermediates in alkyl-aryl kumada coupling reactions

Iron-catalyzed alkyl-aryl Kumada coupling has developed into an efficient synthetic method, yet its mechanism remains vague. Here, we apply a bis(oxazolinylphenyl)amido pincer ligand (Bopa) to stabilize the catalytically active Fe center, resulting in isolation and characterization of well-defined iron complexes whose catalytic roles have been probed and confirmed. Reactivity studies of the iron complexes identify an Fe(II) "ate" complex, [Fe(Bopa-Ph)(Ph)2]-, as the active species for the oxidative addition of alkyl halide. Experiments using radical-probe substrates and DFT computations reveal a bimetallic and radical mechanism for the oxidative addition. The kinetics of the coupling of an alkyl iodide with PhMgCl suggests that formation of the "ate" complex, rather than oxidative addition, is the turnover-determining step. This work provides insights into iron-catalyzed cross-coupling reactions of alkyl halides.

Cross-coupling of nonactivated primary and secondary alkyl halides with aryl Grignard reagents catalyzed by chiral iron pincer complexes

Iron(III) bisoxazolinylphenylamido (bopa) pincer complexes are efficient precatalysts for the cross-coupling of nonactivated primary and secondary alkyl halides with phenyl Grignard reagents. The reactions proceed at room temperature in moderate to excellent yields. A variety of functional groups can be tolerated. The enantioselectivity of the coupling of secondary alkyl halides is low.

Chiral lanthanide complexes: Coordination chemistry, spectroscopy, and catalysis

The coordination chemistry and catalytic applications of organometallic and related lanthanide complexes bearing chiral oxazoline ligands is an area that has been largely underdeveloped, in comparison to complexes based upon lanthanide triflates for use i

Near-IR luminescent neodymium complexes: Spectroscopic probes for hydroamination catalysis

Neodymium complexes bearing the sensitising bis(oxazolinylphenyl)amine (BOPA) ligands have been prepared, and analysed spectroscopically under both catalytic and pseudo-catalytic conditions with respect to the intramolecular hydroamination of an aminoalke

Facile synthesis of C2-symmetric tridentate bis(thiazoline) and bis(oxazoline) ligands and their application in the enantioselective Henry reaction

A series of novel C2-symmetric bis(thiazoline) ligands with a diphenylamine backbone as a linkage between two thiazoline rings were synthesized by the use of the simple reagent phosphorus pentasulfide. Their application in the catalytic asymmet

Coupling of bulky, electron-deficient partners in aryl amination in the preparation of tridentate bis(oxazoline) ligands for asymmetric catalysis

A new class of tridentate bis(oxazoline) ligands 7, in which an N-phenylaniline unit links the two oxazoline rings, has been prepared. The key step in their synthesis is a Hartwig-Buchwald type Pd-catalyzed aryl amination between the two bulky o-substituted coupling partners, 2-(2′-bromophenyl)oxazolines 8 and 2-(o-aminophenyl)oxazolines 9. By varying the substituent on the coupling partners, a range of 10 ligands has been prepared in good yield. During the synthesis of 2-(o-aminophenyl)oxazolines 9a-d, a number of products of unexpected side reactions were isolated in two of the three steps. Alternatively, the required 2-(o-aminophenyl)oxazolines 9 were obtained by a DAST-promoted cyclodehydration of hydroxyamides 12a-d without formation of any byproducts.