Aryl halide

Summary

In organic chemistry, an aryl halide (also known as haloarene) is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications. Classification according to halide Aryl chlorides Aryl chlorides are the aryl halides produced on the largest scale commercially: 150,000 tons/y in the US alone (1994). Production levels are decreasing owing to environmental concerns. Chlorobenzenes are used mainly as solvents. Friedel-Crafts halogenation or "direct chlorination" is the main synthesis route. Lewis acids, e.g. iron(III) chloride, catalyze the reactions. The most abundantly produced aryl halide, chlorobenzene, is produced by this route:

Official source

https://en.wikipedia.org/wiki/Aryl_halide

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Versatile palladium-catalyzed double carbonylation of aryl bromides

Paul Joseph Dyson, Cornel Fink, Gabor Laurenczy

A versatile palladium-catalyzed double carbonylation of aryl bromides has been developed. Using Pd(OAc)2/BuPAd2 as the catalyst system and DBU as the base, under relatively low CO pressure, various a-ketoamides were produced in good yields. In order to get insight into the reaction pathway, real time NMR studies were performed as well and a correlated reaction mechanism is been given.

2017

One-Pot, Three-Component Arylalkynyl Sulfone Synthesis

Chia-Chun Chen, Jérôme Waser

A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO.SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A broad range of aryl and heteroarylalkynyl sulfones were obtained in 46-85% overall yield.

2015

This manuscript covers two main topics. The first part dealt with the organocatalytic conjugate addition of Michael donors to phenyl vinyl selenone. The enantioselective Cinchona alkaloid-catalyzed Michael addition using a-substituted a-nitroacetates has been developed. The synthesis of various a,a-dialkyl a-nitroacetates has been accomplished in excellent yield and good enantioselectivity which were subsequently converted to cyclic and acyclic quaternary a-amino acids, taking advantage of the rich functionalities of the adducts. a-Substituted a-nitroamides have also been utilized as nucleophile. With them, an organocatalytic Michael addition/intermolecular SN2/hydrolysis sequence have been developed for the synthesis of a-lactones in moderate enantioselectivity. The second part of the manuscript focused on the transition-metal-catalysed insertion of isocyanides bearing participating functional group for the synthesis of heterocycles and natural product. On the one hand, the synthesis of 3,5,5-trisubstituted imidazolones using silver-catalyzed reaction of a,a-disubstituted a-isocyanoacetate with primary amine have been developed. To illustrate this methodology, evodiamine and rutaecarpine, two natural products, have been synthesized using methyl o-isocyanobenzoate. The synthesis of 2,3,5,5-tetrasubstituted imidazolones have been also reported using the 3-CR reaction of a,a-dibenzyl a-isocyanoacetate, primary amine and aryl iodide in the presence of a palladium/copper bimetallic system. On the other hand, palladium catalysed isocyanide insertion have been explored. The Pd-catalyzed multicomponent reaction of primary amine, aryl halide and o-cyanobenzonitrile has permitted the construction of 2-substituted quinazolin-4-one. Finally, the Pd-catalyzed domino process isocyanide insertion/C(sp)3-H activation of 3-cyclopropyl-2-isocyanopropanoate furnished C-2 arylated azaspiro[2.4]hept-4-ene.

EPFL2017