105073-81-2

Upstream product

• 16982-67-5 sodium salt of indole 
• 585-71-7 (1-bromoethyl)benzne 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 98-83-9 isopropenylbenzene 
• 1000682-72-3 3-(1-phenyl-2-(phenylselanyl)ethyl)-1H-indole 
• 917-54-4 methyllithium 
• 120-72-9 indole 
• 1295507-23-1 2-(1-(1H-indol-3-yl)ethyl)phenol 
• 1295507-51-5 C₁₇H₁₄F₃NO₃S 
• 90-02-8 salicylaldehyde 
• 695-84-1 2-allylphenol 
• 1579291-74-9 2-(2-azidophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-42-5 styrene 

Relevant academic research and scientific papers

Catalytic Tandem and One-Pot Dehydrogenation-Alkylation and -Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes

The ruthenium-hydride catalyst has been successfully used for the tandem sp3 C-H dehydrogenation-alkylation reaction of saturated hydrocarbon substrates with alcohols to form the alkyl-substituted alkene and arene products. The analogous one-pot dehydrogenation-insertion of saturated ketones with alkenes and dienes directly yielded synthetically useful 2-alkylphenol and benzopyran products in a highly regio- and stereoselective manner without forming any wasteful byproducts. (Chemical Equation Presented).

Control of the Chemoselectivity of Metal N-Aryl Nitrene Reactivity: C-H Bond Amination versus Electrocyclization

A mechanism study to identify the elements that control the chemoselectivity of metal-catalyzed N-atom transfer reactions of styryl azides is presented. Our studies show that the proclivity of the metal N-aryl nitrene to participate in sp3-C-H bond amination or electrocyclization reactions can be controlled by either the substrate or the catalyst. Electrocyclization is favored for mono-β-substituted and sterically noncongested styryl azides, whereas sp3-C-H bond amination through an H-atom abstraction-radical recombination mechanism is preferred when a tertiary allylic reaction center is present. Even when a weakened allylic C-H bond is present, our data suggest that the indole is still formed through an electrocyclization instead of a common allyl radical intermediate. The site selectivity of metal N-aryl nitrenes was found to be controlled by the choice of catalyst: Ir(I)-alkene complexes trigger electrocyclization processes while Fe(III) porphyrin complexes catalyze sp3-C-H bond amination in substrates where Rh2(II) carboxylate catalysts provide both products.

Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics

A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.

Rapid and general protocol towards catalyst-free friedel-crafts C-alkylation of indoles in water assisted by microwave irradiation

An efficient and simplified protocol for uncatalyzed FriedelCrafts alkylation of indoles using microwave irradiation in water is described. A series of functionalized indole derivatives has been synthesized in very short times with moderate to good yields. The combination of microwave irradiation and superheated water offers significant advantages over conventional methods, such as higher selectivities, simplicity, shorter reaction times, and no need for a catalyst.

One-pot oxidative carbon-carbon bond formation of 3-benzylic and 3-allylic indoles with carbon nucleophiles

Indolenines were generated at -78 °C from 3-benzylic or 3-allylic indoles by dehydrogenation with N-tert-butylbenzenesulfinimidoyl chloride, and a carbon-carbon bond was formed at -78 °C in a one-pot manner by treating these indolenines with various carbon nucleophiles such as active methylene compounds or organocuprates.

Novel Bronsted acid catalyzed three-component alkylations of indoles with N-phenylselenophthalimide and styrenes

(Chemical Equation Presented) Novel and efficient Bronsted acid (p-TsOH) catalyzed inter- and intramolecular Friedel-Crafts alkylations have been developed to synthesize selenated three-component coupling and selenation-cyclization indole derivatives. Chemical removal of the phenylseleno moiety was investigated, and the reaction mechanisms were discussed.

Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles

Friedel-Crafts reaction of indoles with α-amido sulfones in the presence of montmorillonite K-10 leads unexpectedly to 3-(1-arylsulfonylalkyl) indoles in good yield. The obtained products can be further desulfonylated under reductive or alkylative conditi

Tandem hydroformylation/Fischer indole synthesis: A novel and convenient approach to indoles from olefins

(Matrix presented) A novel one-pot synthesis of indole systems via tandem hydroformylation/Fischer indole synthesis starting from olefins and arylhydrazines is described. This tandem procedure leads directly to 3-substituted indoles if unsubstituted phenylhydrazine is used and to 3,5- respectively 3,7-disubstituted indoles if para- or ortho-substituted arylhydrazines are used.

Studies of Chiral Indoles. Part I. Indoles with Chiral 1- and 3-Substituents. Synthesis and Preparative Enantiomeric Separation by Chromatography on Microcrystalline Triacetylcellulose

A number of indole derivatives with chiral substituents in position 1 or 3 and with substituents of varying size in position 2 have been prepared.The chiral rotors are 1-N,N-dimethylcarbamoylethyl and N'-methylpiperidin-2'-on-3'-yl and their corresponding thioanalogues, and 1-phenylethyl.The reaction conditions required to obtain preferential 1- or 3-alkylation are discussed in terms of the HSAB principle and the extent of ion pair formation.Three 1-(N,N-dimethylcarbamoylethyl-indoles (R2=H and Me, and R2=Me, R3=CO2Me, R5=OMe) and one 1-(1-phenylethyl)indole (R2=Me, R3=CO2Me, R5=OMe) were obtained optically pure by stereospecific pathways.The other compounds were obtained in racemic forms.Most of the racemic compounds were conveniently resolved by liquid chromatography on swollen, microcrystalline triacetylcellulose (TAC).In some cases rather remarkable separations were obtained.Attempts were made to prepare the optically active 1- and 3-(N'-methylpiperidin-2'-on-3'-yl)indoles by hydrolysis of the methylthioimmonium salts prepared from chromatographically resolved thioamides.The 3-substituted analogues were partly racemized in this process, while the 1-substituted ones were completely racemized.A possible explanation is proposed.