Topic
Friedel–Crafts reaction
About: Friedel–Crafts reaction is a research topic. Over the lifetime, 5183 publications have been published within this topic receiving 86582 citations. The topic is also known as: Friedel-Crafts reaction.
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867 citations
TL;DR: In this tutorial review, recent progress in the development of chiral Brønsted acid-catalyzed asymmetric Friedel-Crafts reactions is presented.
Abstract: The asymmetric Friedel–Crafts reaction is one of the most powerful methods to synthesize optically active aromatic compounds. Particularly, the Friedel–Crafts alkylation of arenes with unsaturated compounds activated by chiral Bronsted acids provides direct access to enantiopure aromatic derivatives with perfect atom economy. In this tutorial review, recent progress in the development of chiral Bronsted acid-catalyzed asymmetric Friedel–Crafts reactions is presented.
645 citations
TL;DR: Alkylation with Activated Alkenes and Carbonyl Compounds in Copper Complexes and Other Metal Complexes: The Incubation Period 2904-2904 3.2.1.
Abstract: 2. The Incubation Period 2904 3. Alkylation with Activated Alkenes 2905 3.1. Copper Complexes 2905 3.2. Other Metal Complexes 2907 3.3. Organocatalysis 2907 4. Alkylation with Carbonyl Compounds 2908 4.1. Copper Complexes 2908 4.2. Other Metal Complexes 2909 4.3. Organocatalysis 2910 5. Alkylation with Imines 2911 5.1. Copper Complexes 2911 5.2. Organocatalysis 2912 6. Miscellaneous 2913 7. Conclusion and Perspectives 2914 8. Acknowledgments 2914 9. Note Added in Proof 2914 10. References 2914
638 citations
TL;DR: Recent developments in the design and use of catalytic and stereoselective strategies for the alkylation of aromatic systems and synthesis of a wide range of polyfunctionalized enantiomerically enriched compounds are reviewed.
Abstract: After more than 125 years, the Friedel-Crafts alkylation is still one of the most studied and most utilized reactions in organic synthesis. What is the secret of this astonishing success? Perhaps the great versatility in scope and applicability continues to justify its crucial role in the synthesis of more and more complex molecules. However, it has taken more than a century for asymmetric catalytic versions of this reaction to be developed and subsequently extended to a range of aromatic compounds and alkylating agents. Herein we review recent developments in the design and use of catalytic and stereoselective strategies for the alkylation of aromatic systems and synthesis of a wide range of polyfunctionalized enantiomerically enriched compounds.
591 citations
TL;DR: The new catalytic approaches described in this review are favoured over classical Friedel–Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides and only low catalyst loadings are needed to provide a wide range of products.
Abstract: The development of efficient Friedel–Crafts alkylations of arenes and heteroarenes using only catalytic amounts of a Lewis acid has gained much attention over the last decade. The new catalytic approaches described in this review are favoured over classical Friedel–Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides. Additionally, only low catalyst loadings are needed to provide a wide range of products. Following a short introduction about the origin and classical definition of the Friedel–Crafts reaction, the review will describe the different environmentally benign substrates which can be applied today as an approach towards greener processes. Additionally, the first diastereoselective and enantioselective Friedel–Crafts-type alkylations will be highlighted.
481 citations