42353-94-6Relevant articles and documents
Trisubstituted alkenes from alkynes and aryl iodides by boron-to-zinc transmetallation and palladium(0) catalyzed cross coupling
Agrios, Konstantinos A.,Srebnik, Morris
, p. 15 - 19 (1993)
Alkenylethylzincs, obtained from the corresponding trialkenylboranes by transmetallation with diethylzine, couple with aryl iodides in the presence of Pd(PPh3)4, 0.19-0.28 molpercent, to produce trisubstituted alkenes in good isolated yields.Both the transmetallation and subsequent coupling occur with complete retention of stereochemistry.
Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst
Genin, Emilie,Michelet, Véronique,Genêt, Jean-Pierre
, p. 3820 - 3830 (2004)
The versatile preparation of trisubstituted alkenes via selective Rh-catalyzed arylation of alkynes is described in water and in a water/toluene biphasic system. For hydrophobic alkyl alkynes, the reaction afforded either alkenes or dienes depending on the temperature and the solvent conditions. Aryl, heteroaryl, silylated and alkyl substituted alkynes reacted equally well with various boronic acids, leading regioselectively to functionalized alkenyl derivatives in high yields (65-99%). The mechanism was investigated in toluene/water mixture or water and involves a vinylrhodium complex. The efficient recycling of the Rh/m-TPPTC system is disclosed with excellent yield (92-96%) and purity of the alkene.
P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
Xiong, Wenrui,Xu, Guangqing,Yu, Xinhong,Tang, Wenjun
, p. 4003 - 4013 (2019/06/24)
Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.
Hydrophenylation of internal alkynes with boronic acids catalysed by a Ni-Zn hydroxy double salt-intercalated anionic rhodium(III) complex
Hara, Takayoshi,Fujita, Nozomi,Ichikuni, Nobuyuki,Wilson, Karen,Lee, Adam F.,Shimazu, Shogo
, p. 863 - 868 (2016/02/18)
[Rh(OH)6]3- intercalated Ni-Zn mixed basic salt (Rh/NiZn) acts as an efficient catalyst for the hydrophenylation of internal alkynes with arylboronic acids under mild conditions. The turnover number per Rh site approached 740 in the reaction between 4-octyne and phenylboronic acid. The catalytic monomeric Rh(iii) complex is stabilised within the NiZn interlayers, attributable to a strong electrostatic interaction, promoting its re-use.