1666-96-2Relevant articles and documents
PALLADIUM-CATALYZED SYNTHESIS OF QUINOLINES FROM ALLYLIC ALCOHOLS AND o-IODOANILINE
Larock, Richard C.,Kuo, Mann-Yan
, p. 569 - 572 (1991)
The palladium-catalyzed coupling of allylic alcohols and o-iodoaniline provides a convenient, one-step synthesis of quinolines.
SBA-15-type organosilica with 4-mercapto-N,N-bis-(3-Si-propyl)butanamide for palladium scavenging and cross-coupling catalysis
El Hankari, Samir,El Kadib, Abdelkrim,Finiels, Annie,Bouhaouss, Ahmed,Moreau, Joel J.E.,Crudden, Cathleen M.,Brunel, Daniel,Hesemann, Peter
, p. 8984 - 8994 (2011)
This work describes the synthesis of novel functional silica materials with difunctional thiol-amide substructures and featuring regular architectures on a mesoscopic level. The functional materials were synthesised by both one-pot co-condensation and post-grafting approaches. The thiol groups confined in the matrix were found to be efficient for palladium entrapment, leading to highly active and reusable heterogeneous catalysts for Sonogashira and Suzuki-Miyaura cross-coupling reactions. This work evidences the crucial role of both the thiol precursor and the condensation degree of the silica scaffold in view of the design of stable and reusable tailor-made mesoporous catalytic silica materials.
Imidazolium supported palladium-chloroglycine complex: Recyclable catalyst for Suzuki-Miyaura coupling reactions
Karthikeyan, Parasuraman,Vanitha, Arumugam,Radhika, Pachaiappan,Suresh, Kannan,Sugumaran, Arunachalam
, p. 7193 - 7197 (2013)
1-Glycyl-3-methyl imidazolium chloride-palladium(II) complex [[Gmim]Cl-Pd(II)] was found to be a catalyst for the Suzuki-Miyaura reaction with excellent yields with high turnover number (6.5 × 102-9.4 × 102).
Pd Nanoparticles Dispersed on ZrIV Organophosphonate: A Robust and Reusable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions
Borah, Suchibrata,Mishra, Shashank,Cardenas, Luis,Gogoi, Nayanmoni
, p. 751 - 758 (2018)
A mesoporous zirconium(IV) phosphonate was synthesized by the hydrothermal reaction of ZrOCl2·8H2O with a trisphosphonic acid ligand, mesityl-1,3,5-tris(methylenephosphonic acid). Treatment of the mesoporous ZrIV phosphonate framework with Pd(OAc)2 and subsequent reduction produced a nanocomposite where Pd nanoparticles of average size ca. 7–8 nm were found to be homogeneously and abundantly dispersed over the phosphonate framework. The composite acts as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross coupling reaction of aryl bromides with aryl boronic acids.
Reusable polymer-supported palladium catalysts: An alternative to tetrakis(triphenylphosphine)palladium in the suzuki cross-coupling reaction
Fenger, Isabelle,Le Drian, Claude
, p. 4287 - 4290 (1998)
The Suzuki cross-coupling reaction of a boronic acid and a bromoaromatic requires palldium catalysis. Almost identical yields were obtained in the usual conditions, with 30 mequiv. of Pd(PPh3)4, and with 2 mequiv of a polymer-supported catalyst, which was easily prepared in two steps from Merrified polymer. Recovery and reuse of the catalyst is easy, and only 0.60% of the initial amount of palladium is lost during a reaction.
From the grafting of NHC-based Pd(II) complexes onto TiO2 to the in situ generation of Mott-Schottky heterojunctions: The boosting effect in the Suzuki-Miyaura reaction. Do the evolved Pd NPs act as reservoirs?
De Tovar, Jonathan,Rataboul, Franck,Djakovitch, Laurent
, p. 133 - 147 (2021/05/10)
The assumption that the real active species involved in the Suzuki-Miyaura reaction are homogeneous, heterogeneous or both is often proposed. However a lack of characterization of the true catalytic entities and their monitoring makes assumptions somewhat elusive. Here, with the aim of getting new insights into the formation of active species in the Suzuki-Miyaura reaction, a family of palladium(II) complexes bearing bis(NHC) ligands was synthesized for immobilization at the surface of TiO2. The studies reveal that once the complexes are anchored onto TiO2, the mechanism governing the catalytic reaction is different from that observed for the non-anchored complexes. All complexes evolved to Pd NPs at the surface of TiO2 under reaction conditions and released Pd species in the liquid phase. Also, this reactivity was boosted by the in situ generation of Mott-Schottky heterojunctions, opening new routes towards the design of heterogenized catalysts for their further implementation in reverse-flow reactors.
Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines
Dherange, Balu D.,Kelly, Patrick Q.,Levin, Mark D.,Liles, Jordan P.,Sigman, Matthew S.
supporting information, p. 11337 - 11344 (2021/08/16)
Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.
