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The Buchwald-Hartwig Amination After 25 Years
Ruth Dorel1, Christian P Grugel2, Alexander M Haydl3
1Stratingh Institute for Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Angewandte Chemie (International Ed. in English)
|June 6, 2019
Summary
The Buchwald-Hartwig amination, a palladium-catalyzed reaction, efficiently forms carbon-nitrogen bonds. This review covers 25 years of its development and applications in organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Palladium-catalyzed coupling reactions are crucial for forming carbon-heteroatom bonds.
- The Buchwald-Hartwig amination specifically targets the formation of C(sp2)-N bonds, a key linkage in many organic molecules.
Purpose of the Study:
- To review the historical development of the Buchwald-Hartwig amination over the past 25 years.
- To highlight recent advancements and applications of this significant cross-coupling reaction.
Main Methods:
- Review of seminal and recent literature on palladium-catalyzed amination reactions.
- Analysis of the evolution from early aminostannane coupling to modern tin-free protocols.
Main Results:
- The Buchwald-Hartwig amination has evolved from specialized methods to a versatile and widely applicable synthetic tool.
- Significant progress has been made in developing practical, tin-free protocols with broad substrate scope.
Conclusions:
- The Buchwald-Hartwig amination remains a cornerstone methodology in modern organic synthesis for C-N bond formation.
- Continued research expands its utility and application in synthesizing complex molecules.
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