395083-12-2Relevant academic research and scientific papers
An easy access to styrenes: Trans aryl 1,3-, 1,4- and 1,5-dienes, and 1,3,5-trienes by Hiyama cross-coupling catalyzed by palladium nanoparticles
Chatterjee, Tanmay,Dey, Raju,Ranu, Brindaban C.
experimental part, p. 1103 - 1110 (2011/07/08)
A convenient and efficient procedure has been developed for the vinylation of aryl-, styrenyl-, cinnamyl- and dienyl-halides by a Pd(0) nanoparticle-catalyzed Hiyama cross-coupling to provide the corresponding dienes and trienes in high yields. The reaction does not require any ligand or co-catalyst, and is carried out using PdCl2 and tetrabutyl ammonium fluoride (TBAF) in THF. Pd nanoparticles are generated in situ and are the active catalytic species in this reaction. A wide range of functionalized styrenes, trans aryl 1,3-, 1,4- and 1,5- dienes, 1,2-, 1-3 and 1,4-bis(1,3-dienes), and 1,3,5-trienes can be obtained by this procedure. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011.
Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
Molander, Gary A.,Brown, Adam R.
, p. 9681 - 9686 (2007/10/03)
We have previously reported that the palladium-catalyzed cross-coupling reaction of potassium vinyltrifluoroborate with aryl electrophiles proceeds with good yields. Herein, we describe recent progress in optimizing the reaction, as well as outlining the scope and limitations of the reaction. The cross-coupling reaction can generally be effected using 2 mol % of PdCl2 and 6 mol % of PPh3 as a catalyst system in THF/H2O with Cs 2CO3 as a base. Moderate to good yields are obtained in the presence of a variety of functional groups.
Suzuki cross-coupling reactions of potassium alkenyltrifluoroborates
Molander, Gary A.,Rivero, Marta Rodriguez
, p. 107 - 109 (2007/10/03)
(formula presented) The palladium-catalyzed coupling reaction of potassium alkenyltrifluoroborates with aryl or alkenyl halides or triflates proceeds readily with good yields. The trifluoroborates are air-and moisture-stable solids that can be stored indefinitely. The cross-coupling can be effected using PdCl2(dppf)-CH2Cl2 as the catalyst in n-PrOH in the presence of Et3N. A variety of functional groups are tolerated. ? Dedicated to Professor Herbert C. Brown on the occasion of his 90th birthday.
