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.
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.
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(
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.
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.
Synthesis and catalytic activity of palladium complexes bearingN-heterocyclic carbenes (NHCs) and 1,4,7-triaza-9-phosphatricyclo[5.3.2.1]tridecane (CAP) ligands
Beli?, Marek,Cazin, Catherine S. J.,Martynova, Ekaterina,Nolan, Steven P.,Scattolin, Thomas,Vanden Broeck, Sofie M. P.,Voloshkin, Vladislav A.
, p. 9491 - 9499 (2021)
The synthesis and characterization of novel palladium complexes bearingN-heterocyclic carbenes (NHCs) and 1,4,7-triaza-9-phosphatricyclo[5.3.2.1]tridecane (CAP) are reported. These organometallic complexes can be easily obtained using two different synthetic strategies that involve either the substitution of the pyridine ligand fromtrans-[Pd(NHC)(Py)Cl2] or by simple addition of the CAP ligand to dimeric species [Pd(NHC)Cl2]2. The mixed NHC/CAP complexes were tested as pre-catalysts in the Buchwald-Hartwig aryl amination coupling, showing good catalytic activity, especially in the case ofcis-[Pd(IPr)(CAP)Cl2].
Design of a Multiuse Photoreactor To Enable Visible-Light Photocatalytic Chemical Transformations and Labeling in Live Cells
Bissonnette, Noah B.,Ryu, Keun Ah,Reyes-Robles, Tamara,Wilhelm, Sharon,Tomlinson, Jake H.,Crotty, Kelly A.,Hett, Erik C.,Roberts, Lee R.,Hazuda, Daria J.,Jared Willis,Oslund, Rob C.,Fadeyi, Olugbeminiyi O.
, p. 3555 - 3562 (2020)
Despite the growing use of visible-light photochemistry in both chemistry and biology, no general low-heat photoreactor for use across these different disciplines exists. Herein, we describe the design and use of a standardized photoreactor for visible-li
Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines
Tao, Shao-Kun,Chen, Shan-Yong,Feng, Mei-Lin,Xu, Jia-Qi,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua,Zheng, Xue-Li,Yu, Xiao-Qi
supporting information, p. 1011 - 1016 (2022/02/05)
The introduction of amines onto aromatics without metal catalysts and chemical oxidants is synthetically challenging. Herein, we report the first example of an electrochemical cross-dehydrogenative aromatization (ECDA) reaction of saturated cyclohexanones and amines to construct anilines without additional metal catalysts and chemical oxidants. This reaction exhibits a broad scope of cyclohexanones including heterocyclic ketones, affording a variety of aromatic amines with various functionalities, and shows great potential in the synthesis of biologically active compounds.
Reagent and Catalyst Capsules: A Chemical Delivery System for Reaction Screening and Parallel Synthesis
Borlinghaus, Niginia,Kaschel, Johannes,Klee, Johanna,Haller, Vanessa,Schetterl, Jasmin,Heitz, Stephanie,Lindner, Tanja,Dietrich, Justin D.,Braje, Wilfried M.,Jolit, Anais
, p. 1357 - 1370 (2020/12/21)
Commercially available hydroxypropyl methylcellulose capsules are employed as a fast, safe, and user-friendly chemical delivery system containing all reagents (catalyst, ligand, and base) for three important transition-metal-catalyzed reactions: Buchwald-Hartwig, Suzuki-Miyaura, and metallophotoredox C-N cross-coupling reactions. This encapsulation methodology simplifies the screening of reaction conditions and the preparation of compound libraries using parallel synthesis in organic solvents or aqueous media. These reagents-containing HPMC capsules are easy to prepare, come in different sizes, and can be stored on the bench under noninert conditions.
