19936-20-0Relevant academic research and scientific papers
Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates
Zhou, Jianrong Steve,Huang, Xiaolei,Teng, Shenghan,Chi, Yonggui Robin
supporting information, p. 3933 - 3936 (2021/04/26)
Nickel-catalyzed Heck reaction of cycloalkenes delivers unusual conjugated arylated isomers. Nickel(0) catalysts ligated by chelating dialkylphosphines effectively activate not only aryl triflates as electrophiles, but also less reactive aryl mesylates, t
Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands
Lauer, Matthew G.,Thompson, Mallory K.,Shaughnessy, Kevin H.
, p. 10837 - 10848 (2015/01/08)
The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
Selective arylation at the vinylic site of cyclic olefins
Wu, Xiaojin,Zhou, Jianrong
supporting information, p. 4794 - 4796 (2013/06/05)
Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.
Palladium-catalyzed C-C bond formation of arylhydrazines with olefins via carbon-nitrogen bond cleavage
Zhu, Ming-Kui,Zhao, Jun-Feng,Loh, Teck-Peng
supporting information; experimental part, p. 6308 - 6311 (2012/01/06)
The unactivated carbon-nitrogen bond of various aryl hydrazines was cleaved under very mild conditions by Pd(0) with the assistance of Pd(II). The in situ generated aryl palladium complex readily takes part in the C-C bond formation with olefins. This study offered a new mode of C-Pd bond formation, which will spur the development of palladium-catalyzed cross-coupling in the future.
A one-pot preparation of aryl- and heteroarylcycloalkenes: Application to the total synthesis of (±)-laurokamurene B
Tallineau, Jean,Bashiardes, Georges,Coustard, Jean-Marie,Lecornué, Frédéric
experimental part, p. 2761 - 2764 (2010/03/03)
A general one-pot method has been developed for the preparation of various aryl- and heteroarylcycloalkenes. After lithiation of aryl and heteroaryl bromides followed by transmetalation with CeCl3, the organocerium addition to cycloalkanones proceeds clea
Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates
Amatore, Muriel,Gosmini, Corinne,Perichon, Jacques
, p. 989 - 992 (2007/10/03)
A new method for the preparation of styrene derivatives is described on the basis of the activation of aryl halides by low-valent cobalt species. A combination of CoII bromide and 2,2′-bipyridine is suitable as catalyst for the cross-coupling reaction of a wide range of aromatic halides (X = Cl, Br, I), mostly bearing sensitive moieties, with vinyl acetates. These reactions proceed under mild conditions in the presence of the appropriate reducing agent to afford α-substituted styrene compounds in satisfactory to high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
