5414-80-2

Upstream product

• 13362-63-5 4-styryl-quinoline 
• 106-45-6 para-thiocresol 
• 100-44-7 benzyl chloride 
• 3262-89-3 triphenylboroxine 
• 1309579-41-6 4-(2-methoxyethyl)quinoline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 100-51-6 benzyl alcohol 
• 91-22-5 quinoline 
• 860346-40-3 N-(quinolin-4-ylmethyl)-N-benzylamine 
• 2785-29-7 benzyl potassium 

Downstream Products

• 102664-38-0 4-(1-benzyl-2-phenyl-ethyl)-quinoline 
• 1619994-29-4 3-phenethyl-3-(2-(N-methylamino)-2-oxoethyl)-indoline-2-thione 

Relevant academic research and scientific papers

Manganese catalyzed C-alkylation of methylN-heteroarenes with primary alcohols

C-Alkylations of nine different classes of methyl-substitutedN-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(i)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon source. The diversifiedN-heteroarenes (41 examples) were isolated in high yields and selectivities. Water is produced as the sole byproduct, making the protocol environmentally benign.

Direct C-H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents

A direct and convenient method for the C-H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.

Skeletal editing through direct nitrogen deletion of secondary amines

Synthetic chemistry aims to build up molecular complexity from simple feedstocks1. However, the ability to exert precise changes that manipulate the connectivity of the molecular skeleton itself remains limited, despite possessing substantial potential to expand the accessible chemical space2,3. Here we report a reaction that ‘deletes’ nitrogen from organic molecules. We show that N-pivaloyloxy-N-alkoxyamides, a subclass of anomeric amides, promote the intermolecular activation of secondary aliphatic amines to yield intramolecular carbon–carbon coupling products. Mechanistic experiments indicate that the reactions proceed via isodiazene intermediates that extrude the nitrogen atom as dinitrogen, producing short-lived diradicals that rapidly couple to form the new carbon–carbon bond. The reaction shows broad functional-group tolerance, which enables the translation of routine amine synthesis protocols into a strategy for carbon–carbon bond constructions and ring syntheses. This is highlighted by the use of this reaction in the syntheses and skeletal editing of bioactive compounds.

Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcoholsviaC-H bond activation

The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping of the enamine intermediate1a'are of special importance.

Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols

In this study, we developed a catalytic system for the C-alkylation of a methyl group on N-heteroaromatic compounds, including pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols based on a hydrogen-borrowing process with [Cp*IrCl2]2 (Cp*: η5-pentamethylcyclopentadienyl) combined with potassium t-butoxide and 18-crown-6-ether as the catalyst precursor.

Ligand-Free RuCl3-Catalyzed Alkylation of Methylazaarenes with Alcohols

RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation, and hydrogenation reaction pathway.

Iridium-catalyzed alkylation of methylquinolines with alcohols

Iridium-catalyzed alkylation of methylquinolines at the methyl substituent was achieved using alcohols as alkylating agents. The reaction proceeded through a transfer hydrogenation pathway from the alcohol to the Ir complex, affording an aldehyde and Ir-H species, followed by base-assisted aldol condensation and hydrogenation. This method provides an atom-economical and convenient route to alkylquinolines from easily accessible methylquinolines.

Ruthenium-catalyzed conversion of sp3 C-O bonds in ethers to C-C bonds using triarylboroxines

Catalytic conversion of unreactive sp3 C-O bonds in alkyl ethers to C-C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C-C bonds.