113845-69-5Relevant articles and documents
Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald-Hartwig Amination
Mizusaki, Tomoteru,Matsumoto, Kazuhiro,Takeuchi, Katsuhiko,Fukaya, Norihisa,Takagi, Yukio,Choi, Jun-Chul
, p. 1872 - 1876 (2019)
An immobilized N-heterocyclic carbene (NHC)-Pd complex was prepared via direct silyl linker installation onto the imidazole backbone of commercially available 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) ligand. The IPr backbone was lithiated and treated with Me2SiCl2 to afford ClMe2Si-IPr, which reacted with [Pd(π-allyl)Cl]2 to yield a ClMe2Si-IPr-Pd complex, and this was immobilized on Wang resin. The immobilized NHC-Pd complex facilitated quantitative Buchwald-Hartwig amination of aryl chlorides within 10 min, even at a low Pd loading of 0.2 mol %. The catalyst could be removed from the reaction mixture by simple filtration, and Pd leaching into the reaction medium was suppressed to below 1 ppm.
A Selective C?H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine
Sundalam, Sunil K.,Nilova, Aleksandra,Seidl, Thomas L.,Stuart, David R.
, p. 8431 - 8434 (2016)
Described here is an efficient method to access highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts. The iodonium salts are prepared in a single pot from either commercially available aryl iodides or arylboronic acids. The
Mixed Phosphite-Phosphine and Phosphinite-Phosphine Palladacyclic Complexes as Highly Active Catalysts for the Amination of Aryl Chlorides
Bedford, Robin B.,Blake, Michael E.
, p. 1107 - 1110 (2003)
Tri-tert-butylphosphine adducts of orthopalladated phosphite and phosphinite complexes formed in situ are excellent catalysts for the Buchwald-Hartwig amination of aryl chloride substrates.
Palladium(II) Complexes with Anionic N-Heterocyclic Carbene-Borate Ligands as Catalysts for the Amination of Aryl Halides
Winkler, Andrea,Brandhorst, Kai,Freytag, Matthias,Jones, Peter G.,Tamm, Matthias
, p. 1160 - 1169 (2016)
A series of (allyl)palladium(II) complexes of anionic N-heterocyclic carbenes that contain a weakly coordinating borate moiety (WCA-NHC) were prepared by deprotonation of the carbene IPr with n-butyllithium in the 4-position, which was followed by addition of B(C6F5)3 and reaction of the resulting lithium carbene-borate with [(η3-allyl)Pd(μ-Cl)]2 (allyl = 2-propenyl, 2-butenyl, 2-methyl-2-propenyl, 1-phenyl-2-propenyl). In polar solvents such as tetrahydrofuran, chloropalladate complexes of the type [Li(THF)3][(WCA-NHC)PdCl(η3-allyl)] were formed, whereas the reactions in toluene afforded neutral complexes of the type [(WCA-NHC)Pd(η3-allyl)], which exhibit an intramolecular interaction with the N-aryl groups of the carbene ligands. The allyl-palladium complexes were employed as catalysts for the Buchwald-Hartwig amination of various aryl halides with morpholine.
Carbocyclic carbene ligands in palladium-catalyzed C-N coupling reactions
Taubmann, Christian,Tosh, Evangeline,?fele, Karl,Herdtweck, Eberhardt,Herrmann, Wolfgang A.
, p. 2231 - 2236 (2008)
Palladium complexes bearing a cycloheptatrienylidene ligand are powerful precatalysts for C-N coupling reactions. Their catalytic performance is directly compared to analogous 2,3-diphenylcyclopropenylidene complexes. The crystal structure of cis-dibromo(
Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis
Martin, Anthony R.,Makida, Yusuke,Meiries, Sebastien,Slawin, Alexandra M. Z.,Nolan, Steven P.
, p. 6265 - 6270 (2013)
Seven new air- and moisture-stable nickel complexes bearing flexible bulky NHC (N-heterocyclic carbene) ancillary ligands (NHC = IPr, IPrTol, IPrOMe, IPent) are reported. Using experimentally determined crystal structures, the steric
Energy-Efficient Solar Photochemistry with Luminescent Solar Concentrator Based Photomicroreactors
Cambié, Dario,Dobbelaar, Jeroen,Riente, Paola,Vanderspikken, Jochen,Shen, Chong,Seeberger, Peter H.,Gilmore, Kerry,Debije, Michael G.,No?l, Timothy
, p. 14374 - 14378 (2019)
The sun is the most sustainable light source available on our planet, therefore the direct use of sunlight for photochemistry is extremely appealing. Demonstrated here, for the first time, is that a diverse set of photon-driven transformations can be efficiently powered by solar irradiation with the use of solvent-resistant and cheap luminescent solar concentrator based photomicroreactors. Blue, green, and red reactors can accommodate both homogeneous and multiphase reaction conditions, including photochemical oxidations, photocatalytic trifluoromethylation chemistry, and metallaphotoredox transformations, thus spanning applications over the entire visible-light spectrum. To further illustrate the efficacy of these novel solar reactors, medicinally relevant molecules, such as ascaridole and an intermediate of artemisinin, were prepared as well.
Coupling of boronic acids with amines in the presence of a supported copper catalyst
Debreczeni, Nora,Fodor, Anna,Hell, Zoltan
, p. 1547 - 1551,5 (2014)
An efficient heterogeneous catalytic method was developed for Chan-Lam reaction, coupling of amines and boronic acid. Copper on 4 A molecular sieve provided yields comparable to the methods published. The method provides the main advantages of a heterogeneous catalytic procedure, the preparation of the catalyst is easy, the workup of the reaction mixture is simple. Graphical abstract: [Figure not available: see fulltext.]
Well-defined allylnickel chloride/N-heterocyclic carbene [(NHC)Ni (allyl)Cl] complexes as highly active precatalysts for C-N and C-S cross-coupling reactions
Iglesias, Maria Jose,Prieto, Auxiliadora,Nicasioa, M. Carmen
, p. 1949 - 1954 (2010)
The room temperature Buchwald-Hartwig amination of heteroaromatic chlorides has been achieved using the sterically bulky allylnickel chloride/ N-heterocyclic carbene [(IPr)Ni (allyl)Cl]complex as a well-defined precatalyst. Arylation of aromatic thiols, affording high yields of products under low catalyst loadings, has also been promoted with the same complex.
Efficient C-N and C-S bond formation using the highly active [Ni(allyl)Cl(IPr*OMe)] precatalyst
Martin, Anthony R.,Nelson, David J.,Meiries, Sebastien,Slawin, Alexandra M.Z.,Nolan, Steven P.
, p. 3127 - 3131 (2014)
Two new [Ni(allyl)Cl(NHC)] complexes with the bulky yet flexible N-heterocyclic carbene (NHC) ligands IPr* {N,N'-bis[2,6- bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene} and IPr* OMe {N,N'-bis[2,6-bis(diphenylmethyl)-4-methoxyphenyl]imidazol-2- ylidene} are reported. These complexes were employed in the amination and sulfination of aryl halide species and were shown to perform well in these reactions, which typically required less than half as much catalyst as previous state-of-the-art nickel complexes. Copyright
