620-84-8Relevant articles and documents
Palladium(II)-acetylacetonato complexes with mesoionic carbenes: Synthesis, structures and their application in the Suzuki-Miyaura cross coupling reaction
Hettmanczyk, Lara,Schmid, Bianca,Hohloch, Stephan,Sarkar, Biprajit
, (2016)
A series of novel palladium(II) acetylacetonato complexes bearing mesoionic carbenes (MICs) have been synthesized and characterized. The synthesis of the complexes of type (MIC)Pd(acac)I (MIC = 1-mesityl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (1), 1,4-(2,4,6-methyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (2), 1,4-(2,6-diisopropyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (3); acac = acetylacetonato) via direct metalation starting from the corresponding triazolium iodides and palladium(II) acetylacetonate is described herein. All complexes were characterized by 1H- and 13C-NMR spectroscopy and high resolution mass spectrometry. Additionally, two of the complexes were characterized by single crystal X-ray crystallography confirming a square-planar coordination geometry of the palladium(II) center. A delocalized bonding situation was observed within the triazolylidene rings as well as for the acac ligand respectively. Complex 2 was found to be an efficient pre-catalyst for the Suzuki-Miyaura cross coupling reaction between aryl-bromides or -chlorides with phenylboronic acid.
Synthesis of 3-aryl-2-phosphinoimidazo[1,2-: A] pyridine ligands for use in palladium-catalyzed cross-coupling reactions
Tran, Ryan Q.,Jacoby, Seth A.,Roberts, Kaitlyn E.,Swann, William A.,Harris, Nekoda W.,Dinh, Long P.,Denison, Emily L.,Yet, Larry
, p. 17778 - 17782 (2019)
3-Aryl-2-phosphinoimidazo[1,2-a]pyridine ligands were synthesized from 2-aminopyridine via two complementary routes. The first synthetic route involves the copper-catalyzed iodine-mediated cyclizations of 2-aminopyridine with arylacetylenes followed by palladium-catalyzed cross-coupling reactions with phosphines. The second synthetic route requires the preparation of 2,3-diiodoimidazo[1,2-a]pyridine or 2-iodo-3-bromoimidazo[1,2-a]pyridine from 2-aminopyridine followed by palladium-catalyzed Suzuki/phosphination or a phosphination/Suzuki cross-coupling reactions sequence, respectively. Preliminary model studies on the Suzuki synthesis of sterically-hindered biaryl and Buchwald-Hartwig amination compounds are presented with these ligands.
On the efficiency of two-coordinate palladium(0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides
Arentsen, Katherine,Caddick, Stephen,Cloke, F. Geoffrey N.
, p. 9710 - 9715 (2005)
The catalytic activity of novel two-coordinate palladium N-heterocyclic carbene complexes that differ in their steric and electronic properties is compared in catalytic amination and Suzuki-Miyaura cross-couplings.
Improved Buchwald-Hartwig Amination by the Use of Lipids and Lipid Impurities
Bayer, Annette,Gevorgyan, Ashot,Hopmann, Kathrin H.
supporting information, (2021/11/12)
The development of green Buchwald-Hartwig aminations has long been considered challenging, due to the high sensitivity of the reaction to the environment. Here we show that food-grade and waste vegetable oils, triglycerides originating from animals, and natural waxes can serve as excellent green solvents for Buchwald-Hartwig amination. We further demonstrate that amphiphiles and trace ingredients present in triglycerides as additives have a decisive effect on the yields of Buchwald-Hartwig aminations.
Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction
Absalan, Yahya,Ghandi, Khashayar,Gholizadeh, Mostafa,Kovalchukova, Olga,Mahmoudi, Ghodrat,Sarvestani, Hossein Sabet,Shad, Nazanin Noroozi,Strashnov, Pavel
, (2021/05/21)
Nine novel Schiff bases were derived from salicylic aldehyde and oxalic aldehyde, isolated, and their molecular and spatial structure were explored by a set of experiments (IR, CNMR, HNMR, CHN, SEM, XRD) and theoretical simulation (DFT def2-TZVP). A high potential was predicted in metal cations chelating. The isolated organic species were applied as the ligands in the reaction of complex formation with titanium (III) chloride and (IV) bromide and 12 novel complexes were synthesized and studied experimentally and theoretically. Using the UV–vis spectroscopic titration, the solution stability of the complexes was indicated. Depending on the nature of the Schiff base ligand, their formation constants were calculated in the range of 6.84–17.32. Using the DFT def2-TZVP theoretical method together with the experimental spectroscopic data, the coordination types of the ligands were investigated, and the structure of the complexes was proposed. The photocatalytic ability of the isolated complexes was tested in the C-N cross-coupling reaction under sunlight. Complexes exhibited high visible-light photocatalytic activity for a wide range of aromatic and benzylic amines including electron-withdrawing and electron-donating groups from moderate to good yields ranging in 50–85 %. The use of an inexpensive, clean, and renewable energy source (visible light) is the superiority of the developed photocatalytic systems.