458529-83-4

Upstream product

• 3377-71-7 N-benzylindole 
• 6773-29-1 dimethyl diazomalonate 
• 104819-24-1 1-benzylindole-3-acetic chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 120-72-9 indole 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 1221496-91-8 monomethyl (N-benzyl-3-indolyl)malonate 

Relevant academic research and scientific papers

Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition

The synthesis of versatile scaffold indolopyrans based on C-C radical-radical cross-coupling under metal-free conditions is described. The reaction involving single electron transfer between coupling partners followed by cage collapse allows highly selective cross-coupling while employing only equimolar amounts of coupling partners. Moreover, the mechanistic manifold was expanded for the functionalization of enamines to give the stereoselective synthesis of 2,3-dihydrofurans. This iodine-mediated oxidative coupling features mild conditions and fast reaction kinetics.

Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles

A Schiff-base nickel(II)-phosphene-catalyzed chemodivergent C-H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.

Direct functionalization of indoles: Copper-catalyzed malonyl carbenoid insertions

Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C-H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2-H insertion product. Microwave conditions are also disclosed which show comparable yields with reduced reaction times.

Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones

A palladium-catalyzed intramolecular decarboxylative cyclization of α-aryl-γ-methylidene-δ-valerolactones, followed by olefin isomerization, has been developed to give fused polycyclic aromatic compounds under mild conditions. The process described here can be regarded as a formal decarboxylative allylic arylation without using a pre-formed organometallic nucleophile. The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease.

Convenient preparation of indolyl malonates via carbenoid insertion

Indoles, when treated with methyldiazomalonate under catalysis by rhodium(II)acetate, undergo C-H and N-H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. In indoles where the 3-position is unsubstituted, hi