Fluorous-Tagged Carbamates for the Pd-Catalyzed Amination of Aryl Halides
- 18 September 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (21) , 8146-8148
- https://doi.org/10.1021/jo701573w
Abstract
A novel fluorous-tagged ammonia surrogate has been synthesized and its application to the synthesis of anilines by Buchwald−Hartwig palladium-catalyzed amidation-hydrolysis protocol is described. Primary anilines were obtained in moderate to good yields after a sequence of two reaction steps involving fluorous separation techniques for their purification. Preliminary results indicate that N-substituted anilines can also be obtained using just N-substituted-FBoc carbamates as the nitrogen source.Keywords
This publication has 21 references indexed in Scilit:
- Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl HalidesJournal of the American Chemical Society, 2006
- Petroleum Marker Dyes Synthesized from Cardanol and Aniline DerivativesIndustrial & Engineering Chemistry Research, 2004
- Amination of aryl halides using copper catalysisTetrahedron Letters, 2001
- Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and MechanismAngewandte Chemie International Edition in English, 1998
- Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylaminesTetrahedron Letters, 1998
- An Ammonia Equivalent for the Palladium-Catalyzed Amination of Aryl Halides and TriflatesTetrahedron Letters, 1997
- Industrial Organic ChemistryPublished by Wiley ,1997
- Halide and Amine Influence in the Equilibrium Formation of Palladium Tris(o-tolyl)phosphine Mono(amine) Complexes from Palladium Aryl Halide DimersOrganometallics, 1996
- Structural Characterization and Simple Synthesis of {Pd[P(o-Tol)3]2}. Spectroscopic Study and Structural Characterization of the Dimeric Palladium(II) Complexes Obtained by Oxidative Addition of Aryl Bromides and Their Reactivity with AminesOrganometallics, 1995
- Synthesis and reaction chemistry of monomeric and dimeric amide complexes of platinum(II)Organometallics, 1991