Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates
- 24 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (6) , 1169-1172
- https://doi.org/10.1021/ol050141b
Abstract
We report that Zn[N(SiMe3)2]2 is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe3)2, the combination of Zn[N(SiMe3)2]2 and LiCl coupled with aryl halides and triflates containing base-sensitive functionality in high yields. In addition, aryl bromides coupled with aryl and alkylamines with the combination of Zn[N(SiMe3)2]2 and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.Keywords
This publication has 33 references indexed in Scilit:
- Fluorescence Resonance Energy Transfer (FRET) as a High-Throughput Assay for Coupling Reactions. Arylation of Amines as a Case StudyJournal of the American Chemical Society, 2003
- Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed ReactionsJournal of the American Chemical Society, 2003
- Scope and Mechanism of Palladium-Catalyzed Amination of Five-Membered Heterocyclic HalidesThe Journal of Organic Chemistry, 2003
- Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room TemperatureAngewandte Chemie International Edition in English, 2002
- Aqueous Hydroxide as a Base for Palladium-Catalyzed Amination of Aryl Chlorides and BromidesThe Journal of Organic Chemistry, 2002
- Palladium-Catalyzed Amination of Aryl Halides and Related ReactionsPublished by Wiley ,2002
- Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-CouplingsThe Journal of Organic Chemistry, 2002
- Practical Palladium Catalysts for C-N and C-O Bond FormationPublished by Springer Nature ,2002
- High Turnover Number and Rapid, Room-Temperature Amination of Chloroarenes Using Saturated Carbene LigandsOrganic Letters, 2000
- Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and MechanismAngewandte Chemie International Edition in English, 1998