23450-31-9

Usage

InChI:InChI=1/C14H11N/c15-11-14-8-6-13(7-9-14)10-12-4-2-1-3-5-12/h1-9H,10H2

Upstream product

• 874-86-2 4-cyanobenzyl chloride 
• 71-43-2 benzene 
• 623-26-7 terephthalonitrile 
• 67-56-1 methanol 
• 10066-31-6 methyl 1-phenyl-2-propyl ether 
• 770-09-2 benzyltrimethylsilane 
• 28493-54-1 benzyltributyltin 
• 98689-33-9 tetramethylammonium triphenylbenzylborate 
• 101-49-5 2-(benzyl)-1,3-dioxolane 
• 4362-18-9 2-benzyl-2-methyl-1,3-dioxolane 
• 2116-36-1 1-benzyl-4-bromo-benzene 
• 544-92-3 copper(I) cyanide 
• 623-03-0 4-Cyanochlorobenzene 
• 108-86-1 bromobenzene 

Downstream Products

• 1503-49-7 p-cyanobenzophenone 
• 100866-27-1 4-benzyl-benzaldehyde seqtrans-oxime 
• 1313757-11-7 1-(bis(4-iodophenyl)methyl)-1H-1,2,4-triazole 
• 1313757-14-0 C₂₁H₁₆N₂O 
• 67468-65-9 4-benzylbenzaldehyde 
• 620-86-0 4-Benzylbenzoic acid 

Relevant academic research and scientific papers

Alkyl-GeMe3: Neutral Metalloid Radical Precursors upon Visible-Light Photocatalysis

Single-electron transfer (SET) oxidation of ionic hypervalent complexes, in particular alkyltrifluoroborates (Alkyl-BF3?) and alkylbis(catecholato)silicates (Alkyl-Si(cat)2?), have contributed substantially to alkyl radical generation compared to alkali or alkaline earth organometallics because of their excellent activity–stability balance. Herein, another proposal is reported by using neutral metalloid compounds, Alkyl-GeMe3, as radical precursors. Alkyl-GeMe3 shows comparable activity to that of Alkyl-BF3? and Alkyl-Si(cat)2? in radical addition reactions. Moreover, Alkyl-GeMe3 is the first successful group 14 tetraalkyl nucleophile in nickel-catalyzed cross-coupling. Meanwhile, the neutral nature of these organogermanes offset the limitation of ionic precursors in purification and derivatization. A preliminary mechanism study suggests that an alkyl radical is generated from a tetraalkylgermane radical cation with the assistance of a nucleophile, which may also result in the development of more non-ionic alkyl radical precursors with a metalloid center.

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C-S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Photoredox Heterobimetallic Dual Catalysis Using Engineered Covalent Organic Frameworks

The functionalization of an imine-based layered covalent organic framework (COF), containing phenanthroline units as ligands, has allowed the obtention of a heterobimetallated material. Photoactive Ir and Ni fragments were immobilized within the porous structure of the COF, enabling heterogeneous light-mediated Csp3-Csp2cross-couplings. As radical precursors, potassium benzyl- and alkoxy-trifluoroborates, organic silicates, and proline derivatives were employed, which brings out the good versatility ofIr,Ni@Phen-COF. Moreover, in all the studied cases, an enhanced activity and stability have been observed in comparison with analogous homogenous systems.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst

The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co

Super electron donor-mediated reductive desulfurization reactions

The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.

Visible-light-mediated external-reductant-free reductive cross coupling of benzylammonium salts with (hetero)aryl nitriles

Herein we report a novel visible-light-mediated external reductant-free reductive cross coupling for the construction of C sp2–C sp3 bonds. A variety of benzylammonium salts underwent selective coupling with (hetero)aryl nitriles to