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

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      Chemical Reviews
      American Chemical Society

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          Abstract

          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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          N-heterocyclic carbenes in late transition metal catalysis.

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            The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates.

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              Biaryl Phosphane Ligands in Palladium-Catalyzed Amination

              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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                Author and article information

                Journal
                Chem Rev
                Chem. Rev
                cr
                chreay
                Chemical Reviews
                American Chemical Society
                0009-2665
                1520-6890
                30 September 2016
                12 October 2016
                30 September 2017
                : 116
                : 19
                : 12564-12649
                Affiliations
                [1]Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States
                Author notes
                Article
                10.1021/acs.chemrev.6b00512
                5070552
                27689804
                4c69a2c3-e106-49d4-90b3-6b7f9f210f70
                Copyright © 2016 American Chemical Society

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                : 03 August 2016
                Categories
                Review
                Custom metadata
                cr6b00512
                cr-2016-00512w

                Chemistry
                Chemistry

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