- Copper-Catalysed Electrophilic Amination of Aryl(alkenyl) Boronic Acids with Nitrogen-Containing Hypervalent Iodine (III) Reagent
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A copper-catalysed electrophilic N-imination of aryl(alkenyl) boronic acids with a stable hypervalent iodine(III) reagent containing a transferable (diarylmethylene)amino group is developed. The electrophilic C?N cross-coupling reaction proceeds smoothly at room temperature under oxidant-free and base-free conditions, which is further characterized by the broad functional group compatibility, thereof, extending the N-electrophile scope of electrophilic C?N cross-coupling outside the limitation of N?O and N?Cl reagents. (Figure presented.).
- Hu, Yuanyuan,Zheng, Songlin,Fan, Wu,Yuan, Weiming
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supporting information
p. 4701 - 4707
(2021/08/23)
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- Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines
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Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.
- Tran, Cong Chi,Kawaguchi, Shin-Ichi,Kobiki, Yohsuke,Matsubara, Hitomi,Tran, Dat Phuc,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
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p. 11741 - 11751
(2019/10/02)
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- Mild conditions for Pd-catalyzed conversion of aryl bromides to primary anilines using benzophenone imine
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Mild (30 °C) and efficient (53-91%) conversion of aryl bromides to primary anilines using a Pd-catalyzed amination strategy is described. A detailed account of the ligand optimization, base and solvent selection, and general substrate scope of this methodology is described herein.
- Bhagwanth, Swapna,Adjabeng, George M.,Hornberger, Keith R.
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experimental part
p. 1582 - 1585
(2009/06/28)
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- Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles
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Resisting pathways for decomposition followed by palladium complexes of monodentate ligands is one characteristic of the highly reactive but long-lived catalyst generated from the Josiphos ligand L and palladium. It catalyzes under mild conditions the coupling of primary amines with chloropyridines and chloroarenes in high yield with low catalyst loadings (see scheme).
- Shen, Qilong,Shekhar, Shashank,Stambuli, James P.,Hartwig, John F.
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p. 1371 - 1375
(2007/10/03)
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- Arylamine synthesis
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The present invention provides a method for the preparation of a wide range of primary arylamines. The arylamines are prepared in two efficient, straightforward transformations: 1) an activated aryl group and an imine group are combined, in the presence o
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