13519-79-4

Upstream product

• 106-95-6 allyl bromide 
• 95-51-2 o-chloroaniline 
• 589-09-3 N-allyl-N-phenylamine 
• 6728-21-8 allyl mesylate 
• 133932-64-6 N-(2-chloro-2-propenyl)-2-chloroaniline 

Downstream Products

• 55245-21-1 C₁₀H₉Cl₂NO 
• 83-34-1 3-Methylindole 
• 1260679-58-0 C₉H₁₀ClN 
• 95-51-2 o-chloroaniline 

Relevant academic research and scientific papers

Syntheses of 3-substituted 2,3-dihydrobenzofuranes, 1,2-dihydronaphtho(2,1-b)furanes, and 2,3-dihydro-1H-indoles by tandem ring closure-SRN1 reactions

3-Substituted 2,3-dihydrobenzofuranes (7a-c), 1,2-dihydronaphtho(2,1-b)furanes (10a-c), and N-substituted 2,3-dihydro-1H-indoles (8a-c, 9a,b) are obtained in very good yields by SRN1 photostimulated reactions in liquid ammonia from adequate haloaromatic compounds orthosubstituted with a suitable double bond (3a,b; 4a,b; 5a; 6a,b) and Me3Sn-, Ph2P-, and -CH2NO2 anions. The novelty of the work involves the versatile application of a 5-exo ring closure process during the propagation cycle of the SRN1 reaction; the alkyl radical intermediates formed react with the nucleophiles to afford the ring closure-substituted heterocycles. The factors governing the observed product distribution are discussed.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

Highly selective N-allylation of anilines under microwave irradiation

An easy and rapid procedure for the preparation of a variety of mono- and bis-allylated anilines via the reaction of allyl bromide with a wide range of anilines under microwave irradiation is described. This approach allows use of mild conditions and short reaction times to give high selectivities and excellent yields.

Efficient copper-catalyzed direct intramolecular aminotrifluoromethylation of unactivated alkenes with diverse nitrogen-based nucleophiles

A mild, convenient, and step-economical intramolecular aminotrifluoromethylation of unactivated alkenes with a variety of electronically distinct, nitrogen-based nucleophiles in the presence of a simple copper salt catalyst, in the absence of extra ligand

Observations on the intramolecular Heck reactions of aromatic chlorides using palladium/imidazolium salts

The intramolecular Heck reaction of aromatic amines and ethers using palladium/imidazolium salts is described. The use of tetra-n-butylammonium halide salts facilitates the reactivity of aromatic chlorides. An unexpected and novel palladium-mediated cyclisation is also described leading to the formation of a tricyclic adduct.

Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base

Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.

Electrocatalytic Coupling of Aryl Halides with (1,2-Bis(di-2-propylphosphino)benzene)nickel(0)

Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides.In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96percent can be obtained with aryl chlorides and 2 mol percent of the title catalyst in polar, coordinating solvents.Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered.Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites.Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.