Matsuda–Heck reaction with arenediazonium tosylates in water

Abstract

SummaryAn environmentally friendly Matsuda–Heck reaction with arenediazonium tosylates has been developed for the first time. A range of alkenes was arylated in good to quantitative yields in water. The reaction is significantly accelerated when carried out under microwave heating. The arylation of haloalkylacrylates with diazonium salts has been implemented for the first time.

Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck–Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

“…18 Not only are they more stable toward chemical decomposition and explosion compared to conventionally used tetrafluoroborates, they are more cleanly prepared by diazotization of respective anilines in the presence of p-toluenesulfonic acid in a variety of polar organic solvents and even water. 19 Hence preparing various arenediazonium tosylates 9 and testing them in the Heck-Matsuda arylation of glutaconic acid dimethyl ester became our primary objective.…”

Magnetically thiamine palladium complex nanocomposites as an effective recyclable catalyst for facile sonochemical cross coupling reaction

“…Methyl (E)‐4‐styryl benzoate; white solid, m. p = 154–156 °C (Lit 158 °C). IR (KBr)/ν (cm −1 ): 3024, 2945, 1708, 1602, 1434, 1277, 1179, 1105, 963, 835, 771, 698, 670, 579.…”

[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles

“…Prepared from 2-diazo-1-(p-tolyl)ethan-1-one (5a) 14 and 4-(trifluoromethyl)benzenediazonium tosylate (4g).…”

“…13 Not only are they more stable toward chemical decomposition and explosion compared to conventionally used tetrafluoroborates, they are more cleanly prepared by diazotization of the respective anilines in the presence of ptoluenesulfonic acid in a variety of polar organic solvents, and even water. 14 As the silver catalyst, we initially selected the readily available silver nitrate. The initial testing of the S. Chuprun et al…”