133363-64-1

Upstream product

• 64097-92-3 2-(1-phenylvinyl)aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 5606-41-7 2-(imino(phenyl)methyl)aniline 
• 1885-29-6 anthranilic acid nitrile 
• 14900-39-1 phenylvinylboronic acid 
• 615-36-1 2-bromoaniline 

Downstream Products

• 727416-65-1 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole 

Relevant academic research and scientific papers

tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines

A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Palladium-Catalyzed Sequential Vinylic C-H Arylation/Amination of 2-Vinylanilines with Aryl boronic Acids: Access to 2-Arylindoles

A palladium-catalyzed selective and successive vinylic C-H arylation/amination of 2-vinylanilines with arylboronic acids to generate indoles has been developed. This procedure represents a straightforward and practical approach to valuable multifunctionalized indoles.

Copper-catalyzed synthesis of N-aryl and N-sulfonyl indoles from 2-vinylanilines with O2 as terminal oxidant and TEMPO as cocatalyst

A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as cocatalyst and O2 as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, res

Metal-free C-H amination for indole synthesis

An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

Copper-catalyzed oxidative amination and allylic amination of alkenes

Enamines and enamides are useful synthetic intermediates and common components of bioactive compounds. A new protocol for their direct synthesis by a net alkene C-H amination and allylic amination by using catalytic Cu II in the presence of MnO2 is reported. Reactions between N-aryl sulfonamides and vinyl arenes furnish enamides, allylic amines, indoles, benzothiazine dioxides, and dibenzazepines directly and efficiently. Control experiments further showed that MnO2 alone can promote the reaction in the absence of a copper salt, albeit with lower efficiency. Mechanistic probes support the involvement of nitrogen-radical intermediates. This method is ideal for the synthesis of enamides from 1,1-disubstituted vinyl arenes, which are uncommon substrates in existing oxidative amination protocols. A new protocol for the direct synthesis of enamides and allylic amines by oxidative N-H/C-H coupling of N-sulfonylanilines with vinylarenes is presented. The reaction works in both inter- and intramolecular modes and is catalyzed by copper salts by using MnO2 as the stoichiometric oxidant (see scheme). Nitrogen heterocycles including indoles, benzothiazine dioxides, and dibenzazepines can be formed. Copyright