Journal ArticleDOI
Study of a new rate increasing "base effect" in the palladium-catalyzed amination of aryl iodides.
Caroline Meyers,Bert U. W. Maes,Kristof T. J. Loones,Gunther Bal,Guy L. F. Lemiere,Roger Dommisse +5 more
TLDR
A general protocol for the intermolecular amination of aryl iodides with all types of amines has been developed based on a standard Pd-BINAP catalyst, using cesium carbonate as the base.Abstract:
Evidence for an interphase deprotonation of Pd(II)−amine complexes with weak carbonate base has been gained for the first time. When a rate-limiting deprotonation step is involved in the catalytic cycle, controlling the structure (shape and size of the particles) and/or molar excess of the carbonate base used can significantly increase the reaction rate of Buchwald−Hartwig aminations. By taking such a “base effect” into account a general protocol for the intermolecular amination of aryl iodides with all types of amines has been developed based on a standard Pd−BINAP catalyst, using cesium carbonate as the base.read more
Citations
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Journal ArticleDOI
Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.
TL;DR: Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts and this review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand.
Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide
TL;DR: In this paper, the selection of the best choice of reaction conditions and ligand of this class for the most commonly encountered and practically important substrate combinations for Pd-catalyzed amination reactions is discussed.
Journal ArticleDOI
Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: scope and structure-activity relationships
TL;DR: These complexes constitute a fourth-generation catalyst for the amination of aryl halides, whose activity complements catalysts based on monophosphines and carbenes, and these data illustrate the benefits of chelation.
Journal ArticleDOI
The Buchwald–Hartwig Amination After 25 Years
TL;DR: This Minireview summarizes the evolution of this cross-coupling reaction over the course of the past 25 years and illustrates some of the most recent applications of this well-established methodology.
Journal ArticleDOI
Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines
Giang D. Vo,John F. Hartwig +1 more
TL;DR: The complex generated from Pd[P(o-tol)(3)](2) and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates, revealing a complementary, if not broader, substrate scope.
References
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Journal ArticleDOI
Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
Adam F. Littke,Gregory C. Fu +1 more
TL;DR: This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.
Journal ArticleDOI
A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines
TL;DR: In this paper, a facile and general catalytic method for the conversion of aryl bromides to arylamines was developed, which works well for inter- and intramolecular processes.
Journal ArticleDOI
Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents
Janis Louie,John F. Hartwig +1 more
TL;DR: In this paper, the reaction of aryl halides with secondary amines in the presence of silylamide base and tri- o -tolyphopshine palladium complexes gives arylamine products.
Journal ArticleDOI
One century of aryne chemistry.
TL;DR: The historical developement of arynes is outlined with an emphasis on recent progress in this challenging field of research, and many aspects of the chemistry of these reactive intermediates are not well understood yet.
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Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents
Janis Louie,John F. Hartwig +1 more