13633-04-0Relevant articles and documents
METHOD FOR PRODUCING ARENE COMPOUNDS AND ARENE COMPOUNDS PRODUCED BY THE SAME
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Paragraph 0121, (2021/06/26)
Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst.
Rhodium-Catalyzed Alkenylation of Toluene Using 1-Pentene: Regioselectivity to Generate Precursors for Bicyclic Compounds
Liebov, Nichole S.,Zhu, Weihao,Chen, Junqi,Webster-Gardiner, Michael S.,Schinski, William L.,Gunnoe, T. Brent
, p. 3844 - 3851 (2019/10/16)
Rhodium catalysts for arene alkenylation reported by our group (e.g., Science 2015, 348, 421; J. Am. Chem. Soc. 2017, 139, 5474; J. Am. Chem. Soc. 2018, 140, 17007) have demonstrated selectivity for 1-aryl alkenes over y-aryl alkenes (y > 1). This selectivity is notable because 1-aryl alkenes or 1-aryl alkanes cannot be generated using acid-based Friedel-Crafts arene alkylation or acidic zeolite catalysts. Herein, we report the extension of Rh arene alkenylation catalysis to generate 1-tolyl-1-pentenes, which are potential precursors for bicyclic compounds. The olefin concentration, copper(II) oxidant identity and concentration, reaction temperature, and rhodium concentration for the alkenylation of toluene with 1-pentene have been optimized using [Rh(Η2-C2H4)2(μ-OAc)]2 as the catalyst precursor. The rhodium-based catalysis achieves up to 12(1):1 anti-Markovnikov selectivity for 1-tolyl-1-pentenes over 2-tolyl-2-pentenes and is selective for alkenylation in the meta and para positions.
Microwave-assisted silica-supported aluminum chloride-catalyzed Friedel-Crafts alkylation
Zupp, Laurine R.,Campanella, Veronica L.,Rudzinski, Diandra M.,Beland, Franois,Priefer, Ronny
, p. 5343 - 5346 (2012/10/30)
Microwave irradiation is a popular method in organic synthesis to achieve high yields in shorter reaction times. This decreases total 'man-hours' in a synthetic setting. Another technique used in organic chemistry to decrease manual manipulations, is solid support reagents. The benefits of this approach is that upon completion of a reaction, a simple filtration can be performed which expedites the work-up and also produces less organic waste. Friedel-Crafts alkylation has been explored using microwave chemistry as well as with solid-supported reagents. In comparison with traditional heating, as well as with AlCl3, superior yields were observed with silica-gel bound aluminum chloride (Si-AlClx) when microwave irradiated for only 5 min.
Catalysis of Friedel-Crafts Alkylation by a Montmorillonite Doped with Transition-Metal Cations
Laszlo, Pierre,Mathy, Arthur
, p. 577 - 586 (2007/10/02)
Catalysts are obtained by exchange of the interstitial cations in the K10 montmorillonite.They are applied to Friedel-Crafts alkylations with halides, alcohols, and olefins.They are quite effective even with unactivated hydrocarbons.Isomer distribution depends little on the catalyst used.Thermodynamic equilibration does not take place, the reactions appear to be kinetically controlled.Efficiency of the catalysts bears no apparent relation to that of the corresponding Lewis acids under homogeneous conditions, and it depends on the nature of the alkylating agent.Zr(IV) and Ti(IV), in general, give the best results.
