2004
DOI: 10.1021/ja045047p
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Enantioselective Synthesis of Six-Membered Palladacycles Having Metal-Bound Stereogenic Carbons:  Isolation and Reactivity of Palladacycles Containing Readily Accessible β-Hydrogens

Abstract: Five enantiopure palladacycles containing palladium bonded to a stereogenic carbon and an N-coordinated oxindole were synthesized by the reaction of alkenyl aryl triflates 2 and 9 with Pd(0) bisphosphine complexes. Two palladacyclic complexes, 3beta and 10alpha, were characterized by single-crystal X-ray crystallography. The reactivity of neutral palladacycles 3beta and 10beta was studied in detail. These unusual palladium alkyls, which have three accessible beta-hydrogens, are thermally stable at temperatures… Show more

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Cited by 39 publications
(13 citation statements)
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“…4 [46]. The Pd(1)-C(17) distance (2.955(4) Å ), which is the shortest distance among those between Pd and carbon atoms of the terminal phenyl ring, is shorter than the sum of van der Waals radii (3.30 Å ) [47].…”
Section: Resultsmentioning
confidence: 99%
“…4 [46]. The Pd(1)-C(17) distance (2.955(4) Å ), which is the shortest distance among those between Pd and carbon atoms of the terminal phenyl ring, is shorter than the sum of van der Waals radii (3.30 Å ) [47].…”
Section: Resultsmentioning
confidence: 99%
“…In a subsequent study, the mechanism of epimerization of the palladium bonded stereocenter in the isolated palladacycles was investigated in more detail (Scheme 10). 17 Palladacycles bearing (R)-BINAP and (R,R)-BDPP ligands were characterized by NMR spectroscopic methods, and in two cases by X-ray crystallographic analyses. The epimerization took place under thermal conditions (above 120 o C), or at room temperature in the presence of weak acids.…”
Section: Methodsmentioning
confidence: 99%
“…It remains Scheme 12 Carbamate-directed, regioselective Mizoroki-Heck reaction by Tamaru [55] Directed Mizoroki-Heck Reactions 183 unclear whether it is the oxygen (shown) or the nitrogen (not shown) functioning as the donor under the basic reaction conditions. Overman isolated stable σ -alkylpalladium(II) complexes, which are stabilized by the nitrogen of a deprotonated N-monosubstituted amide functionality [57][58][59].…”
Section: Scheme 11mentioning
confidence: 99%