Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions
Top Cited Papers
- 7 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (22), 6653-6655
- https://doi.org/10.1021/ja035483w
Abstract
The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C−N bond-forming processes.Keywords
This publication has 14 references indexed in Scilit:
- Palladium-Catalyzed Enantioselective Oxidation of Alcohols: A Dramatic Rate Acceleration by Cs2CO3/t-BuOHOrganic Letters, 2003
- A General and Efficient Copper Catalyst for the Amidation of Aryl HalidesJournal of the American Chemical Society, 2002
- Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium ComplexJournal of the American Chemical Society, 2002
- Practical Palladium Catalysts for C-N and C-O Bond FormationPublished by Springer Nature ,2002
- The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine LigandsAdvanced Synthesis & Catalysis, 2001
- A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen HeterocyclesJournal of the American Chemical Society, 2001
- Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and TriflatesThe Journal of Organic Chemistry, 2000
- A Palladium-Catalyzed Method for the Preparation of Indoles via the Fischer Indole SynthesisJournal of the American Chemical Society, 1999
- A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl ChloridesJournal of the American Chemical Society, 1998
- Sterically Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and Chlorides, and the First Amination of Aryl TosylatesJournal of the American Chemical Society, 1998