The Buchwald–Hartwig Amination After 25 Years

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Abstract

The Pd‐catalyzed coupling of aryl (pseudo)halides and amines is one of the most powerful approaches for the formation of C(sp ²)−N bonds. The pioneering reports from Migita and subsequently Buchwald and Hartwig on the coupling of aminostannanes and aryl bromides rapidly evolved into general and practical tin‐free protocols with broad substrate scope, which led to the establishment of what is now known as the Buchwald–Hartwig amination. 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.

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Paula Ruiz-Castillo, Stephen Buchwald (2016)

Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Biaryl Phosphane Ligands in Palladium-Catalyzed Amination

David Surry, Stephen Buchwald (2008)

Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses the application of these catalysts in C-N cross-coupling reactions in the synthesis of heterocycles and pharmaceuticals, in materials science, and in natural product synthesis.

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Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

David S Surry, Stephen Buchwald, Jeppe Madsen (2011)

Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand of this class for the most commonly encountered and practically important substrate combinations.

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Author and article information

Contributors

Ruth Dorel: (View ORCID Profile)

Christian P. Grugel: (View ORCID Profile)

Alexander M. Haydl: (View ORCID Profile)

Journal

Title: Angewandte Chemie

Abbreviated Title: Angewandte Chemie

Publisher: Wiley

ISSN (Print): 0044-8249

ISSN (Electronic): 1521-3757

Publication date Created: November 25 2019

Publication date (Electronic): September 18 2019

Publication date (Print): November 25 2019

Volume: 131

Issue: 48

Pages: 17276-17287

Affiliations

[1 ] Stratingh Institute for Chemistry Zernike Institute for Advanced Materials University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands

[2 ] Institut für Organische Chemie Albert-Ludwigs-Universität Freiburg Albertstr. 21 79104 Freiburg Germany

[3 ] Department for Intermediates—Amine Synthesis BASF SE Carl-Bosch-Str. 38 67056 Ludwigshafen am Rhein Germany

Article

DOI: 10.1002/ange.201904795

SO-VID: 80431358-5005-4828-9973-d281ef5e2420

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http://onlinelibrary.wiley.com/termsAndConditions#vor

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