72035-50-8

Upstream product

• 65260-38-0 (E)-3-Naphthalen-1-yl-2-phenyl-acrylonitrile 
• 100-51-6 benzyl alcohol 
• 27869-54-1 β-naphthylmethyl-α-phenylacrylonitrile 
• 140-29-4 phenylacetonitrile 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 7677-24-9 trimethylsilyl cyanide 
• 36707-32-1 1-(1-naphthyl)-2-phenylethane 
• 4780-79-4 1-naphthalene methanol 
• 72681-59-5 1-naphthylmethyl 2,2-dimethylpropanoate 

Relevant academic research and scientific papers

Base-controlled chemoselectivity: direct coupling of alcohols and acetonitriles to synthesise α-alkylated arylacetonitriles or acetamides

We achieved chemoselective synthesis of α-alkylated arylacetonitriles and acetamides by combining Ir complex-catalysed direct coupling of alcohols and nitriles by a simple adjustment of the base. Methanol and ethanol performed well as the alkylating reagents. This method of acetonitrile alkylation provided a novel approach for carbon chain extension.

Nickel-catalyzed hydrogen-borrowing strategy: Chemo-selective alkylation of nitriles with alcohols

The first nickel-catalyzed hydrogen-borrowing alkylation of a series of aryl acetonitriles with a variety of aryl, heteroaryl, allylic and alkyl alcohols releasing water as the by-product (>33 examples, up to 90% yield) is reported.

Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis

A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This alkylation reaction uses naturally abundant alcohols and readily available nitriles as coupling partners. The reaction tolerates a wide range of functional groups and heterocyclic moieties, efficiently providing useful cyanoalkylated products with water as the only side product. Importantly, methanol can be used as a C1 source and the chemoselective C-methylation of nitriles is achieved. The mechanistic investigations support the multiple role of the metal-ligand manganese catalyst, the dehydrogenative activation of the alcohol, α-C-H activation of the nitrile, and hydrogenation of the in-situ-formed unsaturated intermediate.

Base-Promoted α-Alkylation of Arylacetonitriles with Alcohols

A practical method to synthesize α-alkylated arylacetonitriles from arylacetonitriles and alcohols without using any expensive transition metal complexes is demonstrated here. Following this base-catalysed sustainable procedure, various arylacetonitriles were successfully alkylated with different alcohols. The practical applicability of this protocol was extended by one-pot synthesis of important carboxylic acid derivatives.

Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay

Direct methods for stereoselective functionalization of sp-hybridized carbon-hydrogen [C(sp3)-H] bonds in complex organic molecules could facilitate much more efficient preparation of therapeutics and agrochemicals. Here, we report a copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C-H bonds into benzylic nitriles. Hydrogen-atom abstraction affords an achiral benzylic radical that undergoes asymmetric C(sp3)-CN bond formation upon reaction with a chiral copper catalyst. The reactions proceed efficiently at room temperature with the benzylic substrate as limiting reagent, exhibit broad substrate scope with high enantioselectivity (typically 90 to 99% enantiomeric excess), and afford products that are key precursors to important bioactive molecules. Mechanistic studies provide evidence for diffusible organic radicals and highlight the difference between these reactions and C-H oxidations mediated by enzymes and other catalysts that operate via radical rebound pathways.

Nickel-Catalyzed α-Benzylation of Arylacetonitriles via C-O Activation

Efficient Ni-catalyzed direct cross-couplings of benzylic alcohol derivatives with arylacetonitriles via C-O activation are described. Various α-benzylated arylacetonitriles including those with functional groups can be prepared under mild reaction conditions.

Water-Soluble Calixarenes as New Inverse Phase-Transfer Catalysts. Their Scope in Aqueous Biphasic Alkylations and Mechanistic Implications

Alkylation reactions of active methylene compounds, alcohols and phenols with alkyl halides in aqueous NaOH solution can be carried out without the need for any added organic solvents in most cases. The water-soluble calix[n]arenes, which contain trimethylammoniomethyl groups on the upper rim, were used as inverse phase-transfer catalysts, resulting in the corresponding alkylated products in good to high yields. The scope of this methodology in aqueous biphasic alkylation reactions and the mechanistic implications are discussed.

Water-soluble calixarenes as new inverse phase-transfer catalysts. Their application to C-alkylations of active methylene compounds in water

Alkylation reactions involving active methylene compounds and alkyl halides in aqueous NaOH solution have been developed by using the water-soluble calix[n]arenes (n = 4, 6 and 8) as inverse phase-transfer catalysts, which contains trimethylammoniomethyl groups on the upper rim.