- A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole
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For the first time, an efficient one-pot method for the construction of an angularly fused 5-6-5 aza-tricyclic framework has been developed in a highly stereoselective manner. This domino reaction is a novel combination of aza-Piancatelli rearrangement an
- Gouse, Shaik,Reddy, Narra Rajashekar,Baskaran, Sundarababu
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- Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
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A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]
- Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao
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- A General Palladium–Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
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The scope and limitations of the monoselective N-arylation of various amines by using aryl and hetaryl tosylates are presented. The air-stable and easily accessible Pd(OAc)2/CM-phos {CM-phos=2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1H-indole}catalyst system was able to deal with a wide range of aryl tosylate substrates as well as amine nucleophiles, including primary and secondary cyclic/acyclic aliphatic amines and anilines. NH-Bearing heterocycles such as indole, carbazole, pyrrole, 10-phenothiazine, and 10-phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst system even offers the opportunity to perform the reaction in water medium. We also report the intermolecular coupling of optically active α-central chiral amines with aryl tosylates without erosion of the enantiomeric purity.
- Choy, Pui Ying,Chung, Kin Ho,Yang, Qingjing,So, Chau Ming,Sun, Raymond Wai-Yin,Kwong, Fuk Yee
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supporting information
p. 2465 - 2474
(2018/09/10)
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- Synchronizing steric and electronic effects in {RuII(NNNN,P)} complexes: The catalytic dehydrative alkylation of anilines by using alcohols as a case study
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A series of new hexacoordinated {RuII(NNNN,P)} complexes was prepared from [RuCl2(R3P)3]. Their structure was determined by X-ray crystallography. The catalytic potential of this new class of complexes was tested in the alkylation of aniline with benzyl alcohol. In this test reaction, the influence of the counteranion plus electronic influences at the tetradentate ligand and the phosphine ligand were examined. The electrochemistry of all complexes was studied by cyclic voltammetry. Depending on the substituent at the ligand backbone, the complexes showed a different behavior. For all N-benzyl substituted complexes, reversible Ru II/III redox potentials were observed, whereas the N-methyl substituted complex possessed an irreversible oxidation event at small scan rates. Furthermore, the electronic influence of different substituents at the ligand scaffold and at the phosphine on the RuII/III redox potential was investigated. The measured E0 values were correlated to the theoretically determined HOMO energies of the complexes. In addition, these HOMO energies correlated well with the reactivity of the single complexes in the alkylation of aniline with benzyl alcohol. The exact balance of redox potential and reactivity appears to be crucial for synchronizing the multiple hydrogen-transfer events. The optimized catalyst structure was applied in a screening on scope and limitation in the catalytic dehydrative alkylation of anilines by using alcohols.
- Weickmann, Daniel,Frey, Wolfgang,Plietker, Bernd
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supporting information
p. 2741 - 2748
(2013/03/14)
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