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CC BY-NC-ND 4.0 · Synthesis 2024; 56(23): 3555-3574
DOI: 10.1055/a-2344-5677
DOI: 10.1055/a-2344-5677
short review
Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions
We are grateful for the financial support provided by the Japan Society for the Promotion of Science (JSPS), through the following grants: Grant-in-Aid for Scientific Research (B) 21H01979, Grant-in-Aid for Transformative Research Areas (A) JP21A204, and the Digitalization-driven Transformative Organic Synthesis (Digi-TOS). We also appreciate support from RIKEN.
Abstract
Palladium- and nickel-catalyzed cross-couplings are powerful methods for constructing C–C and C–N bonds, particularly through Suzuki–Miyaura and Buchwald–Hartwig reactions. Although aryl iodides, bromides, and triflates are the most commonly used substrates, aryl chlorides are less frequently utilized due to their lower reactivity. However, they are appealing because they are readily available and inexpensive. This short review highlights recent developments on the Suzuki–Miyaura and Buchwald–Hartwig cross-couplings of aryl chlorides, using both homogeneous and heterogeneous catalysis with palladium and nickel.
1 Introduction
2 Suzuki–Miyaura Cross-Couplings
2.1 Homogeneous Palladium Catalysis
2.2 Heterogeneous Palladium Catalysis
2.3 Homogeneous Nickel Catalysis
2.4 Heterogeneous Nickel Catalysis
3 Buchwald–Hartwig Amination Reactions
3.1 Homogeneous Palladium Catalysis
3.2 Heterogeneous Palladium Catalysis
3.3 Homogeneous Nickel Catalysis
3.4 Heterogeneous Nickel Catalysis
4 Conclusion
Key words
palladium catalysis - nickel catalysis - cross-coupling - aryl chloride - Buchwald–Hartwig amination - Suzuki–Miyaura coupling - homogeneous catalysis - heterogeneous catalysisPublication History
Received: 30 April 2024
Accepted after revision: 23 May 2024
Accepted Manuscript online:
13 June 2024
Article published online:
08 July 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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