910541-44-5

Upstream product

• 3592-47-0 Benzaldehyde-d 
• 100-46-9 benzylamine 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 122709-84-6 [(E)-Benzylimino]-phenyl-acetic acid 

Downstream Products

• 133167-15-4 2-deuterio-3,5-bis(phenylsulfonyl)-1-benzyl-2-phenyl-1,2,5,6-tetrahydropyridine 
• 1437798-67-8 C₂₁H₁₇⁽²⁾HN₂O 

Relevant academic research and scientific papers

Metal-Ligand cooperation on a diruthenium platform: Selective imine formation through acceptorless dehydrogenative coupling of alcohols with amines

Metal-metal singly-bonded diruthenium complexes, bridged by naphthyridine-functionalized N-heterocyclic carbene (NHC) ligands featuring a hydroxy appendage on the naphthyridine unit, are obtained in a single-pot reaction of [Ru2(CH3COO)2(CO)4] with 1-benzyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazolium bromide (BIN-HBr) or 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazolium bromide (PIN-HBr), TlBF4, and substituted benzaldehyde containing an electron-withdrawing group. The modified NHC-naphthyridine-hydroxy ligand spans the diruthenium unit in which the NHC carbon and hydroxy oxygen occupy the axial sites. All the synthesized compounds catalyze acceptorless dehydrogenation of alcohols to the corresponding aldehydes in the presence of a catalytic amount of weak base 1,4-diazabicyclo[2.2.2]octane (DABCO). Further, acceptorless dehydrogenative coupling (ADHC) of the alcohol with amines affords the corresponding imine as the sole product. The substrate scope is examined with 1 (BIN, p-nitrobenzaldehyde). A similar complex [Ru2(CO) 4(CH3COO)(3-PhBIN)][Br], that is devoid of a hydroxy arm, is significantly less effective for the same reaction. Neutral complex 1 a, obtained by deprotonation of the hydroxy arm in 1, is found to be active for the ADHC of alcohols and amines under base-free conditions. A combination of control experiments, deuterium labeling, kinetic Hammett studies, and DFT calculations support metal-hydroxyl/hydroxide and metal-metal cooperation for alcohol activation and dehydrogenation. The bridging acetate plays a crucial role in allowing β-hydride elimination to occur. The ligand architecture on the diruthenium core causes rapid aldehyde extrusion from the metal coordination sphere, which is responsible for exclusive imine formation. Ligand lends a hand: Metal-hydroxy/hydroxide and metal-metal cooperation is demonstrated for acceptorless dehydrogenation of alcohols to give aldehydes. The ligand architecture ensures rapid extrusion of the aldehyde from the metal core, resulting in the formation of the corresponding imine as the sole coupled product with amines (see scheme; DABCO=1,4-diazabicyclo[2.2.2]octane).

Oxidative radical skeletal rearrangement induced by molecular oxygen: Synthesis of quinazolinones

Oxidative skeletal rearrangement of 5-aryl-4,5-dihydro-1,2,4-oxadiazoles into quinazolinones is induced by molecular oxygen (under a dry air atmosphere) that likely proceeds via transient iminyl radical species. Concise syntheses of biologically active qu

Phosphites mediated decarboxylation of α-iminoacids. A straightforward route to labelled α-aminophosphates

Aminophosphates are of great interest owing to their biological activity. These products are considered as structural analogues of the corresponding aminoacids but also as transition state mimics of peptide hydrolysis. They are known to act as antibiotic and pharmacological agents as well as enzyme inhibitors. Despite the growing importance of these drugs, few methods have been reported for their labelling. These isotopic syntheses usually involve strong bases to generate an α-carbanion which is then quenched with D2O. In the present article we would like to report two novel procedures for the one pot synthesis of labelled α-aminophosphates. These procedures could easily be adapted to tritium labelling.