By Giovanni Sartori
Used within the construction of a large variety of positive chemical substances and prescribed drugs, the Friedel-Crafts acylation response represents a man-made technique of nice curiosity to natural chemists of academia and undefined. approximately forty years because the final significant treatise at the subject and reflecting the starting to be emphasis on green technology, Advances in Friedel-Crafts Acylation Reactions: Catalytic and eco-friendly tactics makes a speciality of the way to make this response extra economically and environmentally pleasant through the use of green acylating stipulations, therefore minimizing the formation of waste and lowering creation costs.
Divided into 4 elements, the ebook explores stoichiometric acylations, catalytic homogeneous acylations, catalytic heterogeneous acylations, and phenol acylations. it really is established in line with the position performed by way of the catalyst within the activation of reagents in addition to within the diversified modes of regioselectivity encountered within the acylation of arenes, fragrant ethers, and phenols.
Incorporating examples of all acid-catalyzed Friedel-Crafts acylation reactions, the textual content considers vintage Lewis and Brönsted acid kinds besides extra cutting edge and complicated multicomponent superacid catalysts. those diversity from infrequent earth triflates or triflimides and their blend with ionic drinks to metal-promoted zeolites and zeotypes, clays, polymetal oxides, sulfated zirconia, heteropoly acids, and Nafion. The booklet emphasizes the key commercial purposes, supplying a severe review of the variations, benefits, and downsides of homogeneous and heterogeneous catalysis.
Helping readers to raised comprehend the mechanism of the Friedel-Crafts acylation, the examples within the booklet substantiate the improvement of more desirable catalysts and extra selective approaches accomplished over the last few a long time, allowing to embark on a more secure and extra effective synthesis of fragrant ketones for the manufacture of a big selection of products.
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Extra info for Advances in Friedel-Crafts Acylation Reactions: Catalytic and Green Processes
2003. Convenient access to polysubstituted 1‑indanones by Sc(OTf)3‑catalyzed intramolecular Friedel–Crafts acylation of benzyl Meldrum’s acid derivatives. Org. Lett. 5: 4653–4656. 24. Sharma, A. , Subramani, A. , and Gorman, C. B. 2007. Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel–Crafts cycliza‑ tion of aryl propionic acids and their use in alkylation reactions. Tetrahedron 63: 389–395. 25. Molloy, B. B. 1979. Trifluoromethyl substituted 1‑aminoindanes. S. Patent 4,132,737.
The bismuth-triflate-catalyzed reaction can be extended to different aromatics as well as to aliphatic and aromatic carboxylic acids, giving ketones in nearly quantitative yield. 06), respectively. The catalyst can be recovered by precipitation with hexane from the final reaction mixture and reused in the benzoylation of meta‑xylene, giving the product with unchanged yield (∼95%) for four successive cycles. 30 By removing water from the reaction mixture by azeotropic distillation and adsorption onto molecular sieves, the yield of benzoylation of para‑xylene with BAC in the presence of perfluorobutanesulfonic acid (10% mol) is improved to 90%.
15. Anderson, K. W. and Tepe, J. J. 2002. The first intermolecular Friedel–Crafts acylation with β‑lactams. Org. Lett. 4: 459–461. 16. Gors, H. , Horner, P. , and Jansons, V. 1991. Friedel–Crafts preparation of aromatic ketones with an inorganic salt controlling agent. S. Patent 5,068,447. 17. Lindley C. R. 1992. BF3 catalyzed acylation of aromatic compounds. EP Patent 488,638. 18. Marshall, W. , Sigmund, S. , and Whitesitt, C. A. 1988. Process for leuko triene antagonists. S. Patent 4,777,299.