51315-69-6

Upstream product

• 593-60-2 Vinyl bromide 
• 589-09-3 N-allyl-N-phenylamine 
• 32704-22-6 2-allyl-phenylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 615-43-0 2-iodophenylamine 
• 73396-92-6 2-iodo-N,N-diallylaniline 
• 1627211-04-4 C₁₅H₁₉N 
• 62-53-3 aniline 

Downstream Products

• 121780-02-7 N-[2-(2-Chloro-3-p-tolylsulfanyl-propyl)-phenyl]-4-methyl-benzenesulfonamide 
• 121780-01-6 N-[2-(2-Chloro-3-phenylsulfanyl-propyl)-phenyl]-4-methyl-benzenesulfonamide 
• 187869-26-7 2,2-bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]-N-(p-toluenesulfonyl)acetamide 
• 173436-68-5 2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 51315-70-9 2-methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 1094359-10-0 (S)-2-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 1170692-63-3 C₂₄H₂₄BrNO₃S 
• 1170692-60-0 C₂₃H₂₂BrNO₂S 
• 1182846-95-2 C₂₃H₂₀INO₃S 
• 33852-38-9 2-benzyl-1-tosylindoline 
• 1251853-79-8 2-(azidomethyl)-1-tosylindoline 
• 1251853-80-1 4-methoxy-N-((1-tosylindolin-2-yl)methyl)aniline 

Relevant academic research and scientific papers

Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant

The palladium-catalyzed aminoazidation of aminoalkenes yielding azidomethyl-substituted nitrogen-containing heterocycles was developed. The procedure requires oxidative conditions and occurs at room temperature in the presence of hydrogen peroxide and NaN3 as the azide source. These conditions provide selective exo-cyclization/azidation of the carbon-carbon double bond, furnishing a versatile approach toward five-, six-, and seven-membered heterocyclic rings.

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.

Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Cycloisomerization of o-Allylanilines Using Organic Redox Cocatalyst

A scalable and practical synthesis of functionalized indoles via Pd-tBuONO cocatalyzed aerobic cycloisomerization of o-allylanilines is reported. Using molecular oxygen as a terminal oxidant, a series of substituted indoles were prepared in moderate to good yields. The avoidance of hazardous oxidants, heavy-metal cocatalysts, and high boiling point solvents such as DMF and DMSO enables this method to be applied in pharmaceutical synthesis. A practical gram-scale synthesis of indomethacin demonstrates its application potential.

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles

The iron-catalyzed synthesis of α-dienyl N-heterocycles is reported. The method is cost-effective, atom-economic, and led to a range of substituted α-dienyl heterocycles in moderate to good yields and diastereoselectivities. The α-dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α-polyenyl N-heterocycles.

Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins

A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)indoles and 2-(2-aminoethyl)pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome.

Copper-Promoted Intramolecular Aminotrifluoromethylation of Alkenes with Langlois Reagent as the Trifluoromethyl Source

A novel approach for copper-promoted intramolecular aminotrifluoromethylation of alkenes using inexpensive CF3SO2Na as the trifluoromethyl source is described. The feature of this method is the concurrent construction of a five-membered ring and a C-CF3 bond in the simple copper salt/TBHP system. A gram-scale reaction was tested with a slight decrease in the yield. This protocol provides an operationally simple, step-economical and synthetically useful access to a variety of trifluoromethyl indolines, pyrrolidines and lactams.