86401-99-2

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 75-64-9 tert-butylamine 
• 125640-89-3 N-(4-fluorobenzyl)-tert-butylamine 
• 119072-55-8 tert-butylisonitrile 
• 352-34-1 4-fluoro-1-iodobenzene 
• 6852-54-6 N-(benzylidene)ethylamine 
• 39769-09-0 4-fluoro-N-[(1E/Z)-(4-fluorophenyl)methylene]aniline 

Downstream Products

• 459-57-4 4-fluorobenzaldehyde 
• 1112208-82-8 2-fluoro-5-formylphenylboronic acid pinacol ester 
• 1844839-22-0 4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 125640-89-3 N-(4-fluorobenzyl)-tert-butylamine 
• 91416-53-4 2-(tert-butyl)-3-(4-fluorophenyl)-1,2-oxaziridine 
• 49834-29-9 N-(tert-butyl)-4-fluorobenzamide 

Relevant academic research and scientific papers

Diastereodivergent [3 + 2] Annulation of Aromatic Aldimines with Alkenes via C-H Activation by Half-Sandwich Rare-Earth Catalysts

Stereodivergent catalysis is of great importance, as it can allow efficient access to all possible stereoisomers of a given product with multiple stereocenters from the same set of starting materials. We report herein the first diastereodivergent [3 + 2]

Convenient fabrication of carbon doped WO3?x ultrathin nanosheets for photocatalytic aerobic oxidation of amines

It is an important chemical transformation for oxidation of amines to imines, on account of very important versatile applications of imines in organic synthesis. Here, we develop a convenient way to synthesize carbon doped WO3?x ultrathin nanos

2D sp2 Carbon-Conjugated Porphyrin Covalent Organic Framework for Cooperative Photocatalysis with TEMPO

2D covalent organic frameworks (COFs) are receiving ongoing attention in semiconductor photocatalysis. Herein, we present a photocatalytic selective chemical transformation by combining sp2 carbon-conjugated porphyrin-based covalent organic framework (Por-sp2c-COF) photocatalysis with TEMPO catalysis illuminated by 623 nm red light-emitting diodes (LEDs). Highly selective conversion of amines into imines was swiftly afforded in minutes. Specifically, the π-conjugation of porphyrin linker leads to extensive absorption of red light; the sp2 ?C=C? double bonds linkage ensures the stability of Por-sp2c-COF under high concentrations of amine. Most importantly, we found that crystalline framework of Por-sp2c-COF is pivotal for cooperative photocatalysis with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO). This work foreshadows that the outstanding hallmarks of COFs, particularly crystallinity, could be exploited to address energy and environmental challenges by cooperative photocatalysis.

Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.

A Metal-Free Approach to 1,2-Diamines via Visible Light-Driven Reductive Coupling of Imines with Perylene as a Photoredox Catalyst

A simple, metal-free, and versatile approach to 1,2-diamines has been developed based on reductive coupling reactions of various imines, where perylene, an aromatic hydrocarbon, was used as a photoredox catalyst under visible light irradiation using a white light-emitting diode. The use of 1 mol % perylene enabled almost complete conversion of the imines, leading to the formation of their corresponding 1,2-diamines, which were isolated in good yields. The ratios between dl and meso diamines ranged from 31:69 to 82:18 depending on the substituents of the imines.

Synthesis of 4-Isoxazolines via Visible-Light Photoredox-Catalyzed [3 + 2] Cycloaddition of Oxaziridines with Alkynes

A method for [3 + 2] cycloaddition of oxaziridines with alkynes to form 4-isoxazolines via visible-light photoredox catalysis is described. This method is a greener, atom-economical reaction that tolerates various functional groups and provides good to excellent yield. Moreover, the cyclization products can be conveniently converted into tetrasubstituted allylic alcohols and enamines. A mechanistic study suggests that the reaction involves photoredox-catalyzed in situ generation of a nitrone from the oxaziridine by SET.

Well-Defined Silica Grafted Molybdenum Bis(imido) Catalysts for Imine Metathesis Reactions

Novel site-isolated tetracoordinated molybdenum complexes possessing bis(imido) ligands, [( - Si-O)2Mo( - NR)2] (R = t-Bu, 2,6-C6H3-i-Pr2), were immobilized on partially dehydroxylated silica (SiO2-200) by a rigorous surface organometallic chemistry protocol. The newly developed materials adorned with bis(imido) functional units, which were previously exploited mainly as spectator ligands on silica-supported olefin metathesis molybdenum catalysts, are found to be efficient heterogeneous catalytic systems for imine cross metathesis under mild conditions.

Structure-Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines

The autoinduced, frustrated Lewis pair (FLP)-catalyzed hydrogenation of 16-benzene-ring substituted N-benzylidene-tert-butylamines with B(2,6-F2C6H3)3 and molecular hydrogen was investigated by kinetic analysis. The pKa values for imines and for the corresponding amines were determined by quantum-mechanical methods and provided a direct proportional relationship. The correlation of the two rate constants k1 (simple catalytic cycle) and k2 (autoinduced catalytic cycle) with pKa difference between imine and amine pairs (ΔpKa) or Hammett's σ parameter served as useful parameters to establish a structure-reactivity relationship for the FLP-catalyzed hydrogenation of imines.

Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines

The ligand-enabled development of ortho and meta C-H borylation of aromatic aldehydes is reported. It was envisaged that while ortho borylation could be achieved using tert-butylamine as the traceless protecting/directing group, meta borylation proceeds via an electrostatic interaction and a secondary interaction between the ligand of the catalyst and the substrate. These ligand-substrate electrostatic interactions and secondary B-N interactions provide an unprecedented controlling factor for meta-selective C-H activation/borylation.

Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors

An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.