Simple, efficient and reusable Pd–NHC catalysts for hydroamination

作者: Qian Chen , Lanlan Lv , Meng Yu , Yanhui Shi , Yuling Li

DOI: 10.1039/C3RA42990C

关键词: Medicinal chemistryHydroaminationCatalysisBromideHomogeneous catalysisReactivity (chemistry)Organic chemistryPhenylacetyleneMarkovnikov's ruleCarbeneChemistry

摘要: A series of chelating NHC–palladium complexes with different alkane-bridges the type Pd[NHC–(CH2)n–NHC]X2 (X = Br or Cl, n 2–4) were synthesized, where NHC is a triazolyl-N-heterocyclic carbene donor ligand. The bromide 2 and 3 characterized by X-ray crystallography. effects length bridge halide ligand on catalytic reactivity in hydroamination reaction investigated. best performance was observed propylene-bridged Pd–NHC complex 2. phenylacetylene 4-methylphenylacetylene various substituted anilines catalyzed yielded only Markovnikov addition products good yield. Interestingly, this homogenous catalyst can be reused three times without significant loss activity.

参考文章(66)
Hyunseok Kim, Tom Livinghouse, Jun Hwan Shim, Seong Guk Lee, Phil Ho Lee, Yttrium(III)‐Catalyzed Intramolecular Alkyne Hydroaminations Advanced Synthesis & Catalysis. ,vol. 348, pp. 701- 704 ,(2006) , 10.1002/ADSC.200505448
Kai?C. Hultzsch, Transition Metal‐Catalyzed Asymmetric Hydroamination of Alkenes (AHA) Advanced Synthesis & Catalysis. ,vol. 347, pp. 367- 391 ,(2005) , 10.1002/ADSC.200404261
Barry M. Trost, Andrew McClory, Rhodium-catalyzed cycloisomerization: formation of indoles, benzofurans, and enol lactones. Angewandte Chemie. ,vol. 46, pp. 2074- 2077 ,(2007) , 10.1002/ANIE.200604183
Michael L. Cooke, Kun Xu, Bernhard Breit, Enantioselective rhodium-catalyzed synthesis of branched allylic amines by intermolecular hydroamination of terminal allenes. Angewandte Chemie. ,vol. 51, pp. 10876- 10879 ,(2012) , 10.1002/ANIE.201206594
Eduardo Peris, Robert H Crabtree, Recent homogeneous catalytic applications of chelate and pincer N-heterocyclic carbenes Coordination Chemistry Reviews. ,vol. 248, pp. 2239- 2246 ,(2004) , 10.1016/J.CCR.2004.04.014
Guy Bertrand, Enrique Díez-Barra, Juan Fernández-Baeza, Heinz Gornitzka, Andrés Moreno, Antonio Otero, René Ignacio Rodríguez-Curiel, Juan Tejeda, Synthesis, Characterization and Dynamic Behavior of Mono- and Dinuclear Palladium(II) Carbene Complexes Derived From 1,1′-Methylenebis(4-alkyl-1,2,4-triazolium) Diiodides European Journal of Inorganic Chemistry. ,vol. 1999, pp. 1965- 1971 ,(1999) , 10.1002/(SICI)1099-0682(199911)1999:11<1965::AID-EJIC1965>3.0.CO;2-K
Christo S. Sevov, Jianrong (Steve) Zhou, John F. Hartwig, Iridium-Catalyzed Intermolecular Hydroamination of Unactivated Aliphatic Alkenes with Amides and Sulfonamides Journal of the American Chemical Society. ,vol. 134, pp. 11960- 11963 ,(2012) , 10.1021/JA3052848