Friedel-Crafts reaction reviews

T. Ohwada, Reactive Carbon Electrophiles in Friedel-Crafts Reactions, Reviews on Heteroatom Chemistry 1995,12, 179. 

Review Problem 6 Some chemists who were investigating the possibility of reversible Friedel-Crafts reactions, wanted an activated aromatic ring cormected to a branched alkyl chain and chose to make TM 82. How would you do it ... 

For a review of the use of isotopic labeling to study Friedel-Crafts reactions, see Roberts, R.M. Gibson, T.L. Isot. Org. Chem., 1980, 5, 103. 

The use of catalytic SILP materials has been reviewed recently [10] covering Friedel-Crafts reactions [33-37], hydroformylations (Rh-catalyzed) [38], hydrogenation (Rh-catalyzed) [39,40], Heck reactions (Pd-catalyzed) [41], and hydroaminations (Rh-, Pd-, and Zn-catalyzed) [42]. Since then, the SILP concept has been extended to additional catalytic reactions and alternative support materials. In this paper we will present results from continuous, fixed-bed carbonylation and hydroformylation reactions using rhodium-based SILP catalysts as reaction examples demonstrating the advantages of the SILP technology for bulk chemical production. 

Metivier, P. Friedel-Crafts Acylation In Friedel-Crafts Reaction Sheldon, R. A. Bek-kum, H. eds., WUey-VCH New York. 2001, ppl61-172. (Review). 

For a comprehensive review of all aspects of the Friedel-Crafts reaction, see G. A. Olah, Ed.,... 

A review entitled Electrophilic species that can react with benzene are dicationic covers the reactions of benzene with several reactive electrophiles and developments in understanding of the mechanism of the Friedel-Crafts reaction.5... 

A short review in Chinese covers Friedel-Crafts reactions of alkenyl halides with aromatic hydrocarbons.49 High yields of the allylated aromatic products have been... 

Friedel-Crafts reactions of aromatic compounds with acyl chlorides, anhydrides, or related compounds in the presence of a Lewis acid have been reviewed [429,430], Among a variety of Lewis acids, the most typical is AICI3, although there are reactions as shown in Eqs (172) [431], (173) [432], and (174) [433] in which TiCU was used as the Lewis acid. 

Chiral titanium complexes are also employed as effective asymmetric catalysts for other carbon-carbon bond-forming reactions, for example addition of diketene (Sch. 66) [154c,162], Friedel-Crafts reaction (Sch. 67) [163] (Sch. 68) [164], iodocar-bocyclization (Sch. 69) [165], Torgov cyclization (Sch. 70) [166], and [2 -i- 1] cycloaddition (Sch. 71) [167]. Asymmetric functional group transformations can also be catalyzed by chiral titanium complexes. These transformations, for example the Sharpless oxidation [168] or hydride reduction [169] are, however, beyond the scope of this review because of space limitations. Representative results are, therefore, covered by the reference list. 

Introduction. In the preceding experiment a general discussion of the Friedel-Crafts reaction was given, which should be reviewed. The object of the present experiment is to illustrate the application of the Friedel-Crafts reaction to the synthesis of simple ketones. 

Reaction of aryl nitrilium ions (40) or imidoyl chlorides (41) with benzonitrile produced the nitrilium species (42), which underwent Friedel-Crafts reaction yielding the quinazoline system (43 Scheme 17). Generation and cyclization of nitrilium species using Friedel-Crafts reagents has since found widespread favor in heteroaromatic synthesis and such procedures have been reviewed in detail. An illustration of its use for a nonbenzenoid aromatic system is given in equation (31). ... 

Another type of solid superacid is based on perfluorinated resin sulfonic acids, such as the acid form of DuPont s Nafion resin, a copolymer of a perfluorinated epoxide and vinylsulfonic acid, or higher perflu-oroalkanesulfonic acids such as perfluorodecanesulfonic acid, CF3(CF2) 03H. Such solid catalysts were found to be very efficient in alkylation of aromatic hydrocarbons and other Friedel-Crafts reactions. A comprehensive review is available on the application of Nafion-H in organic catalysis. ... 

In Chapter 6 we discussed the remarkable mixing effect of Friedel-Crafts reactions. Let us briefly review it and then discuss its application to various aromatic and heteroaromatic compounds (Scheme 8.7). Friedel-Crafts reaction of 1,3,5-trimethoxybenzene with a highly reactive electrochemically generated N-acyliminium ion pool using a conventional macrobatch reactor results in the formation of an essentially 1 1 mixture of the monoalkylation product and the dialkylation product. The reaction is very fast and is complete within Is even at —78°C. 

This section summarises recent work on alkaloids containing the pyrrolidine nucleus. A short review concerning the synthesis of this group has appeared. A variety of Labiatae plants have been screened and some of them have been shown to contain pyrrolidine alkaloids. Cuskhygrine has been found in the roots of three Datura species and stachydrine has been obtained from Capparis spinosa3 The structure of trichostachine (1) Piper trichostachyon) has been elucidated by spectral means and confirmed by synthesis. Ficine (5), an interesting flavonoid alkaloid, has been synthesised. Friedel-Crafts reaction between... 

The well-established stabilization of a positive charge on carbon p to silicon has been utilized in very versatile methods for the control of aliphatic Friedel-Crafts reactions. The specificity of this stabilization lies behind the utility of both alkenyl- and allyl-silanes as substrates for electrophilic substitutions, and acylations in particular. These classes offer complementary regiospecificities in controlling both the site of acylation and the location of the double bond. This promotion of simple substitution is one of the most significant advances in aliphatic Friedel-Crafts acylations of recent times, and has recently been the subject of an exhaustive review. ... 

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