117531-36-9

Upstream product

• 348-54-9 2-Fluoroaniline 
• 106-95-6 allyl bromide 
• 594-19-4 tert.-butyl lithium 
• 1978-38-7 2-fluoro-N-methylaniline 
• 2622-05-1 allylmagnesium bromide 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 475039-72-6 N-allyl-N-(2-bromoallyl)-2-fluoroaniline 
• 1170692-57-5 C₉H₁₀FN 
• 1170692-70-2 C₁₆H₁₆FNO₂S 
• 475040-08-5 1-bromo-5,6-dihydrophenanthridine 
• 475039-81-7 4-bromo-3-methyl-1H-indole 
• 61-50-7 N,N-dimethyltryptamine 
• 928307-78-2 N-allyl-N-(2-bromo-4,5-methylenedioxybenzyl)-2-fluoroaniline 
• 928307-89-5 N-allyl-N-(1-bromo-2-naphthylmethyl)-2-fluoroaniline 
• 475039-97-5 N-allyl-N-(2-bromobenzyl)-2-fluoroaniline 

Relevant academic research and scientific papers

Nickel-Catalyzed Aminofluoroalkylation of Alkenes: Access to Difluoroalkylated N-Containing Heterocyclic Compounds

A nickel-catalyzed aminofluoroalkylative cyclization of unactive alkenes with iododifluoromethyl ketones was developed to construct versatile difluoroalkylated Nitrogen-containing heterocycles including aziridines, pyrrolidines and piperidines in moderate to high yields. This method features a broad substrate scope and has been demonstrated on gram scale.

Facet-Dependent Catalytic Activity of Palladium Nanocrystals in Tsuji-Trost Allylic Amination Reactions with Product Selectivity

Pd nanocubes, cuboctahedra, and octahedra with good size control were used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. Nanocubes gave either monoallylaniline or diallylaniline depending on the amount of allyl bromide used, but the octahedra and cuboctahedra only gave mixtures of monoallylaniline and diallylaniline under the same reaction conditions. The Pd nanocubes were stable over multiple cycles of the reaction. The cubes and octahedra were demonstrated to catalyze the amination reaction by using a wide variety of substituted anilines, but the cubes were the best catalyst with consistently the highest efficiency, product yield, and product selectivity. This work demonstrates that the use of metal nanocrystals with proper facet control is important for catalyzing coupling reactions with product selectivity. Getting into shapes: Pd nanocubes, cuboctahedra, and octahedra with good size control are used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. The Pd nanocube catalyst gives good product selectivity, whereas the Pd octahedra and cuboctahedra catalysts yield mixtures of products under the same reaction conditions. Furthermore, Pd nanocubes are stable over multiple reaction cycles.

Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines

A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is

Palladium-catalyzed selective aminoamidation and aminocyanation of alkenes using isonitrile as amide and cyanide sources

A mild and efficient palladium-catalyzed intermolecular aminoamidation and aminocyanation reaction of alkenes with a broad substrate scope has been developed. This cyclization process provides a valuable synthetic tool for obtaining substituted indolines, tetrahydroisoquinolines and pyrrolidines in good to excellent yields. This journal is

One-pot N-alkylation/Heck approach to substituted indoles

Here, we report the palladium-catalyzed one-pot N-alkylation/Heck cyclization of anilines to substituted indoles employing Pd(OAc)2/XPhos. The scope and limitations of this methodology will be described.

Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization

The synthesis of highly substituted dibenzo-azocine systems is still lacking. An efficient synthetic protocol utilizing the sequential aromatic aza-Claisen rearrangement followed by the implementation of the intramolecular Heck reaction as a key step has been developed for the synthesis of various dibenzo-azocine derivatives of biological relevance.

2-Arylallyl as a new protecting group for amines, amides and alcohols

Amines, amides and ethers containing 2-arylallyl groups are selectively and easily deprotected with tert-butyllithium. This transformation probably involves a carbolithiation reaction of the styrenyl moiety followed by a β-elimination process. The Royal Society of Chemistry 2005.

Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization

The development of a new method for the regioselective synthesis of functionalized indoles and six-membered benzo-fused N-, O-, and S-heterocycles is reported. The key step involves the generation of a benzyne-tethered vinyl or aryllithium compound that undergoes a subsequent intramolecular anionic cyclization. Reaction of the organolithium intermediates with selected electrophiles allows the preparation of a wide variety of indole, tetrahydrocarbazole, dihydrofenantridine, dibenzopyran, and dibenzothiopyran derivatives. Finally, the application of this strategy to the appropriate starting materials allows the preparation of some tryptamine and serotonin analogues.

UNEXPECTED REACTIVITY OF ALLYL MAGNESIUM CHLORIDE WITH NITROARENES. A GENERAL METHOD OF SYNTHESIS OF N-ALLYL-N-ARYLHYDROXYLAMINES AND N-ALLYLANILINES.

In contrast to alkyl Grinard reagents, the allyl reagent reacts with nitroarenes via 1,2 addition to the nitro group.The "in situ" treatment of the unstable intermediate adduct with LiAlH4 in the presence of catalytic Pd/C provides a general synthesis of N-allyl-N-arylhydroxylamines or N-allylanilines.