20423-73-8

Upstream product

• 16077-09-1 5-methoxy-1-methyl-1H-indole-2,3-dione 
• 100-58-3 phenylmagnesium bromide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 39755-95-8 5-methoxyisatine 

Downstream Products

• 1425058-65-6 3-(4-hydroxyphenyl)-5-methoxy-1-methyl-3-phenylindolin-2-one 
• 20423-72-7 1,3-dihydro-5-methoxy-1-methyl-3-phenyl-2H-indol-2-one 

Relevant academic research and scientific papers

Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes

Arynes are highly reactive intermediates, which are utilized for the electrophilic arylation of various X-H bonds (X = O, N, S etc.). Herein, a new synthetic strategy is demonstrated, where arynes are converted into aryl anion equivalents by treatment with phosphines and a base. The addition of phosphines to arynes form the phosphonium salts, which in the presence of a carbonate base generates the aryl anion equivalent. Subsequent addition of the aryl anions with aldehydes afforded the secondary alcohols.

Palladium-catalyzed allylic alkylation with internal alkynes to construct C-C and C-N bonds in water

A palladium-catalyzed system enabled efficient allylic alkylation with alkynes in water has been developed. This reaction presents an environmentally friendly strategy for constructing lots of allylic compounds with indolinones, ketones, amines as well as electron-rich aromatic compounds as nucleophiles. Moreover, the in situ formed arylallene intermediate adopting alkynes as starting materials omits the need for leaving groups and extra oxidants, showing high atom economy. The versatility of the developed reaction also lends itself to the incorporation of deuteriums by simply replacing H2O with D2O.

Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes

An unprecedented palladium-catalyzed allylic alkylation of pronucleophiles with unactivated skipped enynes has been developed. This method provides a straightforward access to a wide array of 1,3-dienes without the need to preinstall leaving groups or employ extra oxidants. The reaction exhibited high atom economy, good functional group tolerance, excellent regioselectivities, and scalability. With D2O as cosolvent, deuterium could be incorporated in high efficiency.

Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Br?nsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Br?nsted acid-catalyzed nucleophilic substitution reaction

Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol- 1-ium intermediate.