118510-01-3Relevant academic research and scientific papers
Unprecedented substoichiometric use of hazardous aryl diazonium salts in the Heck-Matsuda reaction via a double catalytic cycle
Callonnec, Franccois Le,Fouquet, Eric,Felpin, Franccois-Xavier
supporting information; experimental part, p. 2646 - 2649 (2011/06/28)
The first Heck-Matsuda reaction using a catalytic amount of diazonium salts has been discovered. The reaction proceeds through an unprecedented double catalytic cycle in which the electrophile is in situ generated through the reaction advancement. This concept features mild and safe conditions as hazardous aryl diazonium salts are not isolated anymore. Importantly, this sustainable procedure generates only environmentally friendly byproduct such as t-BuOH, H2O, and N2.
Heck cross-coupling of aryldiazonium tetrafluoroborate with acrylates catalyzed by palladium on charcoal
Felpin, Francois-Xavier,Fouquet, Eric,Zakri, Cecile
experimental part, p. 2559 - 2565 (2009/08/14)
A property-activity relationship study of various palladium supported on charcoal (Pd/C) catalysts has been undertaken for the Heck reaction of aryldiazonium tetrafluoroborate with acrylates. The optimized protocol enables the cross-coupling with a low loading of palladium at room temperature in technical grade methanol. Although the catalyst could not be recycled at this time, measurement of the palladium content by inductively coupled plasma mass spectrometry (ICP-MS) shows low palladium contamination of the solvent and product, rendering this method safer for the environment compared to homogeneous conditions.
Cerium(IV)-induced nitration of cinnamic acids. Novel remote electrophilic substitution
Peterson, John R.,Do, Hoang D.,Dunham, Andrew J.
, p. 1670 - 1674 (2007/10/02)
The treatment of (E)-3,4-dimethoxycinnamic acid with ceric amonium nitrate in trifluoroacetic acid afforded (E)1,2-dimethoxy-4-nitro-5-(2-nitroethenyl)benzene in 79percent yield.The unusual ipso substitution of the carboxylic acid moiety by a nitro functional center illustrated a new reaction manifold of cerium(IV).Six cinnamic acids were examined to ascertain the generality of the transformation.The bidentate nitrato structure of the metal salt is believed to account for the nitrating ability of this system.
