73396-91-5

Upstream product

• 107-18-6 allyl alcohol 
• 615-36-1 2-bromoaniline 
• 106-95-6 allyl bromide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 107-11-9 1-amino-2-propene 
• 6728-21-8 allyl mesylate 

Downstream Products

• 601493-67-8 1-methyl-3-ethylindoline 
• 589-09-3 N-allyl-N-phenylamine 
• 4375-15-9 3-methyl-2,3-dihydro-1H-indole 
• 71492-76-7 N-allyl-N-methyl-2-bromoaniline 
• 1048344-57-5 1-allyl-1-(2-bromophenyl)urea 
• 681144-78-5 3-[(2-bromophenyl)(prop-2-enyl)amino]cyclopent-2-en-1-one 
• 21874-23-7 (3-methylindolin-1-yl)(phenyl)methanone 
• 83-34-1 3-Methylindole 

Relevant academic research and scientific papers

Insertion Reaction of 2-Halo- N -allylanilines with K 2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

A synthesis of benzothiazole derivatives through the reaction of 2-halo- N -allylanilines with K 2S in DMF is developed. The trisulfur radical anion S 3· -, which is generated in situ from K 2S in DMF, initiates

1,4-AZABORINE COMPOUNDS AND METHODS OF SYNTHESIS

A compound comprising a structure of formula A

Monobenzofused 1,4-azaborines: Synthesis, characterization, and discovery of a unique coordination mode

We report the first general synthesis of boron-substituted monobenzofused 1,4-azaborines using ring-closing metathesis of an enamine-containing diene as a key synthetic strategy. As part of our investigations, we discovered that the B-C3 moiety in a 1,4-a

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.

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted indoles

(Chemical Equation Presented) Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme). dba = dibenzylideneacetone, dppf = 1,1′-bis(diphenylphospanyl)ferrocene.

Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones

The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to?be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of CuI and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed.

Synthesis of Cyclopenta[b]indol-1-ones and Carbazol-4-ones from N-(2-Halophenyl)-Substituted Enaminones by Intramolecular Heck Reaction

An efficient synthetic route towards N-methylated or nonmethylated 3,4-dihydrocyclopent[b]indol-1(2H)-ones (3) and 1,2,3,9-tetrahydrocarbazol-4(4H)-one (10) was elaborated, based on Pd-catalyzed intramolecular Heck reaction. The chemoselectivity of the cyclization was studied in the case of the bi- and trifunctional substrates 12 and 17, respectively. In the latter case, depending on the catalyst, either the brominated indole 18 or the tetracyclic compound 19 were obtained by single and double Heck reaction, respectively.

Preparation of differentially 1,3-disubstituted indolines by intramolecular carbolithiation

The ether-soluble dilithio species (2), derived from N-allyl-2-bromoaniline (1) upon treatment with t-BuLi at -78°C, cyclizes when warmed to +5°C in the presence of TMEDA to give a (1-lithio-3-indolinyl)methyllithium (3) that may be differentially functio

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.

Catalytic aminomercuration of olefins in a tandem aminomercuration-deoxymercuration; one-step synthesis of secondary n-arylallylamines from allylalcohols

Allyl alcohols react with primary aromatic amines and stoichiometric amounts of mercury(II) tetrafluoroborate to give mixtures of mono- and diallyl anilines. However, the use of the tandem aminomercuration-deoxymercuration promoted by catalytic mercury(II) tetrafluoroborate allows to perform regiospecifically the monoallylation reaction with very high yields. A mechanism is proposed to account for the observed results.