Proton-Catalyzed Hydroamination and Hydroarylation Reactions of Anilines and Alkenes: A Dramatic Effect of Counteranions on Reaction Efficiency
- 28 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (42) , 14542-14543
- https://doi.org/10.1021/ja053700i
Abstract
The anilinium salt, [PhNH3][B(C6F5)4], has been identified as a catalyst for the hydroamination and hydroarylation of several different types of alkenes with anilines. The weakly coordinating counterion of this acid plays a key role in this transformation. The reaction is facile for styrenes and tolerates norbornene, cyclic alkenes, and cyclohexadiene. Selectivity between hydroamination and hydroarylation products can be tuned using reaction time, temperature, and substrate substitution. Details regarding the substrate scope and selectivity of this hydroamination/hydroarylation reaction are discussed.Keywords
This publication has 14 references indexed in Scilit:
- Catalytic Hydroamination of Alkynes and Norbornene with Neutral and Cationic Tantalum Imido ComplexesOrganic Letters, 2004
- TiCl4-Catalyzed Intermolecular Hydroamination Reactions of NorborneneOrganic Letters, 2004
- Chiral Shift Reagent for Amino Acids Based on Resonance-Assisted Hydrogen BondingOrganic Letters, 2004
- Intramolecular Hydroamination Catalyzed by Cationic Rhodium and Iridium Complexes with Bidentate Nitrogen-Donor LigandsOrganometallics, 2004
- Ion Pair Basicity of Some Amines in THF: Implications for Ion Pair Acidity Scales1Journal of the American Chemical Society, 2000
- Palladium-Catalyzed Intermolecular Hydroamination of Vinylarenes Using ArylaminesJournal of the American Chemical Society, 2000
- Catalytic Alkylation of Aromatic Amines with Styrene in the Presence of Cationic Rhodium Complexes and AcidSynlett, 1999
- Metal-Initiated Amination of Alkenes and AlkynesChemical Reviews, 1998
- Zeolite catalysts for the Friedel-Crafts alkylation of methyl benzoate, a strongly deactivated aromatic substratePublished by Elsevier ,1997
- Rhodium-catalysed hydroamination-hydroarylation of norbornene with aniline, toluidines or diphenylamineJournal of Organometallic Chemistry, 1994