58078-54-9Relevant academic research and scientific papers
Heck-Matsuda arylation of olefins through a bicatalytic approach: Improved procedures and rationalization
Oger, Nicolas,Le Callonnec, Francois,Jacquemin, Denis,Fouquet, Eric,Le Grognec, Erwan,Felpin, Francois-Xavier
supporting information, p. 1065 - 1071 (2014/04/03)
The scope of the palladium-catalyzed Heck-Matsuda reaction, proceeding through the catalytic activation of anilines into the corresponding diazonium salts, has been considerably extended and is now working with deactivated electrophiles. Two different procedures, using catalytic amounts of both palladium and acid, have been optimized allowing the concept of bicatalysis to cover the complete electronic range of anilines. These environmentally friendly procedures proceed under very mild conditions, at room temperature in methanol, and only generate tert-butyl alcohol, water and nitrogen as by-products. Rationalization of reaction outcomes encountered in this work has been discussed with the support of computational studies.
Versatile palladium-catalyzed C-H olefination of (hetero)arenes at room temperature
She, Zhijie,Shi, Yang,Huang, Yumin,Cheng, Yangyang,Song, Feijie,You, Jingsong
supporting information, p. 13914 - 13916 (2015/01/09)
The room-temperature oxidative C-H/C-H cross-couplings between (hetero)arenes and alkenes, coumarins or quinones have been reported by using a highly electrophilic palladium species [Pd(TFA)2], generated in situ from Pd(OAc)2and TFA, as the catalyst and cheap (NH4)2S2O8as the oxidant under air.
Non-cross-linked polystyrene-supported triphenylarsonium halides and their use in the arsa-Wittig reaction
Lau, Kelvin C.Y.,Chiu, Pauline
experimental part, p. 8769 - 8774 (2011/12/02)
Non-cross-linked polystyrene-supported (carbomethoxymethyl) triphenylarsonium bromide (1) and benzyltriphenylarsonium iodide (2) were synthesized. They showed similar reactivities compared with the free arsonium salts in the arsa-Wittig reaction. The use of the polymer-supported reagents facilitated product purification and rendered the organoarsenic reagents easily separable and recyclable.
Rhodium-catalyzed double 1,4-addition of arylboronic acids to β-aryloxyacrylates involving β-oxygen elimination
Matsuda, Takanori,Shiose, Shigeru,Suda, Yuya
supporting information; experimental part, p. 1923 - 1926 (2011/10/05)
The rhodium-catalyzed addition reaction of arylboronic acids to β-aryloxyacrylates gives 3,3-diarylpropanoates in good yields. The double arylation reaction proceeds via the intermediate cinnamates generated by β-oxygen elimination. Copyright
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.
One-pot halogenation-Heck coupling reactions in ionic liquids
Handy, Scott T.
, p. 3176 - 3178 (2008/02/13)
Traditional cross-coupling approaches rely upon two steps - halogenation and coupling - each of which is viewed and conducted independently. In an effort to develop a one-pot approach, we have noted that the halogenation and Heck coupling reactions can both be conducted in a room-temperature ionic liquid without the need to isolate the halogenated intermediate. Application to several systems shows that this approach works well for moderately to highly electron-rich aromatics. Georg Thieme Verlag Stuttgart.
