13924-28-2

Upstream product

• 98-80-6 phenylboronic acid 
• 780-20-1 N-benzylidene-4-bromoaniline 
• 586-78-7 para-nitrophenyl bromide 
• 100-51-6 benzyl alcohol 
• 92-67-1 4-phenylalanine 
• 6554-98-9 trans-4-Hydroxystilbene 
• 31656-91-4 4-azidobiphenyl 
• 100-52-7 benzaldehyde 

Downstream Products

• 1169936-48-4 C₂₁H₂₁N 
• 1211-40-1 4-amino-4'-nitrobiphenyl 
• 73842-48-5 N-benzyl-[1,1'-biphenyl]-4-amine 

Relevant academic research and scientific papers

New synthesis, electroluminescence, and photophysical properties of poly[(formylphenyl)methylsilanediyl] and its derivatives

A new one-step synthesis of formylated poly[methyl(phenyl)silanediyl] (PMPSi) is reported. The aldehyde groups were incorporated into the parent polymer by the reaction with dichloromethyl methyl ether in the presence of Lewis acid (SnCl4). The

Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles

The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.

Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives

A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Interrupted imino-nazarov cyclization of 1-aminopentadienyl cation and related cascade process

Facile 4π conrotatory imino-Nazarov cyclization of a 1-aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)-catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indoline-fused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline-fused cyclopentenone in a concise manner. Taking control: The fate of an oxyallyl cation formed through a 4π conrotatory imino-Nazarov cyclization can be controlled to access cyclopentanoid frameworks. In the presence of silver(I), intramolecular arene trapping leads to indoline-fused cyclopentanones. Gadolinium(III) facilitates a cascade transformation to furnish tetrahydroquinoline-fused cyclopentenones. Tf=trifluoromethanesulfonyl.

One-pot preparation of imines from nitroarenes by a tandem process with an Ir-Pd heterodimetallic catalyst

A new tandem catalytic process has been studied for a heterodimetallic complex containing both iridium and palladium fragments connected by a 1,2,4-trimethyltriazolyldiylidene ligand. The process implies the unprecedented preparation of imines from the direct reaction of nitroarenes and primary alcohols. The global process comprises the following steps: 1) reduction of the nitroarene to an amine, 2) oxidation of the alcohol to aldehyde, and 3) condensation of the aldehyde and the amine to form the corresponding imine. The oxidation of the alcohol to aldehyde is promoted by the iridium fragment, while the reduction of the nitro group to amine is facilitated by palladium. A wide set of different catalytic systems has been studied, showing that the Ir/Pd complex 1 is a highly active and stable catalyst in the preparation of imines.

Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions

Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki-Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5 × 105 and turnover frequencies (TOF) of up to 198 000 h-1 for aryl bromides. Aryl chlorides undergo the Suzuki reaction with arylboronic acids with TON of up to 4700 and TOF up to 4700 h-1. Even inexpensive and readily available benzyl and allyl chlorides undergo the coupling reaction with good turnover numbers. Complexes of 12 catalyze the syntheses of symmetrical biaryls in good yields via reductive coupling of iodoarenes in the presence of Huenig's base.