76464-91-0

Upstream product

• 91-73-6 N,N-dibenzylaniline 
• 100-39-0 benzyl bromide 
• 540-37-4 p-aminoiodobenzene 
• 5122-99-6 4-iodophenylboronic acid 

Downstream Products

• 91511-90-9 p-(5-methyl-5-hydroxy-1,3-hexadiynyl)-N,N-dibenzylaniline 
• 1039775-66-0 C₆₀H₆₀N₂O₄ 
• 1197984-72-7 (8S,9S)-9-[4-(dibenzylamino)phenyl]-6'-methoxycinchonan 
• 91-73-6 N,N-dibenzylaniline 
• 1287761-28-7 C₂₉H₂₅NO 
• 82815-80-3 4-(N,N-dibenzylamino)-1-ethynylbenzene 
• 82815-79-0 p-(3-methyl-3-hydroxy-1-butynyl)-N,N-dibenzylaniline 

Relevant academic research and scientific papers

Site-Selective Pd-Catalyzed C(sp3)?H Arylation of Heteroaromatic Ketones

A ligand-controlled site-selective C(sp3)?H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C?H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion.

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions

Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.

Bio-inspired enol-degradation for multipurpose oxygen sensing

Inspired by the enol-degradation of luciferin, a new oxygen sensor with oppositely changed color and fluorescence has been designed. This new reaction-based dual mode sensor can not only be used as a highly selective instant "fluorescence on" oxygen probe, but also as a freshness indicator of food or food materials by using its property of time-adjustable color fading.

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.

Active template synthesis of rotaxanes and molecular shuttles with switchable dynamics by four-component PdII-promoted Michael additions

(Chemical Equation). Taking the Michael: Rotaxanes (see structure) and molecular shuttles are prepared in up to 99% yield by successive Pd II-promoted 1,4-conjugate additions in a one-pot four-component assembly process. This process represents the first active template reaction in which the template motif is retained in the interlocked product.

Amines useful as brain imaging agents

Certain radioiodine containing amines useful as brain imaging agents are disclosed. The compounds of the invention are represented by the formula STR1 wherein I is a radioisotope of iodine with I-123 being preferred, R is lower alkyl or halogen, R1 and R2 are the same or different and are selected from the group consisting of hydrogen and lower alkyl, R3 and R4 are the same or different and are selected from the group consisting of hydrogen, alkyl, aryl, substituted aryl, aralkyl, substituted aralkyl and substituted carbamoyl methyl or R3 and R4 taken together with the nitrogen to which they are attached form a 5- or 6-membered ring which may be substituted with one or more lower alkyl groups, x is 0 to 4, y is 0 to 3 and z is 0 or 1 and pharmaceutically acceptable acid addition salts thereof.