134627-73-9

Upstream product

• 603-76-9 1-methylindole 
• 29546-14-3 4-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N,N-dimethylaniline 
• 50-00-0 formaldehyd 
• 121-69-7 N,N-dimethyl-aniline 
• 52866-87-2 N-((tert-butylperoxy)methyl)-N-methylaniline 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

C-Methylenation of anilines and indoles with CO2and hydrosilane using a pentanuclear zinc complex catalyst

The one-stepC-methylenation of anilines and indoles with CO2and phenylsilane was catalyzed by a pentanuclear ZnIIcomplex to give diarylmethanesviageminal C-H and C-C bond formation. It is proposed that the zinc-hydride complex generatedin situis a catalytically active species and that bis(silyl)acetal is a key intermediate. When aniline was used as a substrate, both theC-methylenation andN-methylation proceeded.

Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

An iridium-catalyzed, highly efficient, and site-selective deoxygenation of primary, secondary, and tertiary alcohols has been realized, under the assistance of a 4-(N-substituted amino)aryl directing group. Only the hydroxyl adjacent to the directing group can be deoxygenated. The deoxygenation is performed in water, with formic acid as both the promoter and hydride donor. Excellent yields and functionality tolerance, as well as high efficiency (S/C up to 1000 000, TOF up to 445 000 h-1), are obtained. The kinetic isotope effect studies show that hydride formation is the rate-determining step, and the deoxygenation follows an SN1-type pathway. The deoxygenation protocol has been demonstrated useful in the structural modification of naturally occurring ketones and steroids.

Metal and acid-free visible light-mediated Friedel-Crafts alkylation reactions of indole with anilines

Metal and acid-free visible light-induced Friedel-Crafts C3-alkylation reactions of indole derivatives were developed using N,N-dimethylanilines as the carbon source. A cheap and readily available organic dye, Rose Bengal, was applied as the photocatalyst. This environmentally friendly transformation afforded C3-alkylated indoles in moderate to good yields under mild conditions.

Visible-Light-Promoted Alkylation of Indoles with Tertiary Amines by the Oxidation of a sp3 C-H Bond

A visible-light driven reaction for the synthesis of 3-arylmethyl indole derivatives using tertiary amines and indoles was first reported. Corresponding products were obtained with yields of up to 70%, and various functional groups on the indoles were well tolerated when Rose Bengal was used as a photosensitizer and air was used as a green oxidant under mild reaction conditions. (Figure presented.).

Ruthenium-catalyzed alkylation of indoles with tertiary amines by oxidation of a sp3 CH bond and lewis acid catalysis

Ruthenium porphyrins (particularly [Ru(2,6-Cl2tpp)CO]; tpp = tetraphenylporphinato) and RuCl3 can act as oxidation and/or Lewis acid catalysts for direct C-3 alkylation of indoles, giving the desired products in high yields (up to 82

A novel multi-component reaction of indole, formaldehyde, and tertiary aromatic amines

A novel multi-component reaction of indoles, formaldehydes, and tertiary aromatic amines is described for the synthesis of dialkylaminoarylated indoles using silica-supported perchloric acid (HClO4-SiO2) as an inexpensive and highly efficient catalyst. The key features of this multi-component reactions are operational simplicity, mild reaction conditions, regioselectivity, and recycling of catalyst.

Benzotriazole: A novel synthetic auxiliary

Benzotriazole and aldehydes react reversibly to give addition products: in the presence of amines and other NH-compounds water can be eliminated to form products of type Bt-CHR-NR′R″. The latter are versatile intermediates for the preparation of primary, secondary, and tertiary amines and in the alkylation of hydroxylamines, hydrazines, amides, thioamides, and sulfonamides. Polyfunctional amines and other polyfunctional compounds can also be prepared, and they enable significant extending of Mannich reaction. Similar oxygen compounds Bt-CRR′-OR″ enable new syntheses of ethers and esters. Reactions in which benzotriazole is eliminated rather than substituted open up new pathways to enamines, enol ethers, and nitrones. The methodology is capable of extension to a variety of vinylogous systems including benzenoid and heteroaromatic derivatives. In addition to acting as a versatile leaving group, benzotriazolyl residues activate neighboring CH bonds to proton loss and a variety of such applications is described.

Benzotriazole as a Synthetic Auxiliary: Advantageous Syntheses of Substituted Diarylmethanes and Heterocyclic Analogues

4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation.Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dy