DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement
作者:Shunpei Ishikawa、Kei Manabe
DOI:10.1002/anie.200905544
日期:2010.1.18
Palladium catalysts bearing dihydroxyterphenylphosphine ligands (such as 1) are reported for the ortho‐selective cross‐coupling of Grignardreagents and dihaloarenes. The second hydroxy group onto the terphenylphosphine ligand dramatically improved the catalytic efficiency and expanded the scope of the reaction.
Ortho-selective Cross Coupling of Dibromophenols and Dibromoanilines with Grignard Reagents in the Presence of Palladium Catalysts Bearing Hydroxylated Oligoarene-type Phosphine
作者:Shunpei Ishikawa、Kei Manabe
DOI:10.1246/cl.2007.1304
日期:2007.11.5
p-Terphenylphosphines with a hydroxy group were used as ligands for palladium in the catalytic cross coupling of dibromophenols and dibromoanilines with Grignard reagents. High ortho-selectivity that cannot be achieved with other phosphine ligands was observed.
Hydroxylated terphenylphosphine ligands for palladium-catalyzed ortho-selective cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents
作者:Shunpei Ishikawa、Kei Manabe
DOI:10.1016/j.tet.2011.09.013
日期:2011.12
p-Terphenylphosphines bearing one or two hydroxy groups were used as ligands to palladium in the cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents. High ortho-selectivity that cannot be achieved using other phosphine ligands was observed. ortho-Preference was also observed in competitive cross-coupling reactions of two substrates. A significant effect of the concentration of the Grignard reagent on the ortho-selectivity was observed, when the hydroxylated terphenylphosphines were used. Kinetic studies on this effect showed that high concentrations of the Grignard reagent retard the cross-coupling reaction only at the para-position, but not at the ortho-position. (C) 2011 Elsevier Ltd. All rights reserved.
Highly Ortho-Selective Cross-Coupling of Dichlorobenzene Derivatives with Grignard Reagents
作者:Shunpei Ishikawa、Kei Manabe
DOI:10.1021/ol702646s
日期:2007.12.1
Highly ortho-selective cross-coupling of dichlorobenzene derivatives with Grignard reagents was realized using a combination of Pd-2(dba)(3) and PCy3. Use of hydroxylated terphenylphosphines further improved the reactions of dichlorophenol and dichloroaniline.
DESCHEPPER, R. E.;SWENTON, J. S., TETRAHEDRON LETT., 1985, 26, N 40, 4831-4834