Chloroaromatics: Advances in Synthesis and Applications

Andrade, Vitor S. C. de; Mattos, Marcio C. S. de

doi:10.1002/9783527827992.ch57

Cited by 4 publications

(1 citation statement)

References 99 publications

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“…Overall, these combinations have demonstrated to be an excellent source of new and highly efficient iodine(III)-base halogenating and nitrating species, which are generated in situ under mild conditions (Scheme 1E) and does not require previous activation or preparation that limits the functional group tolerance, as those already described for similar functionalization. [86][87][88][89] The particular cases of chlorination, bromination, iodination and nitration using this strategic combination of diverse iodine(III) reagents and the aluminum or ammonium salts, are overviewed below. Currently DFT calculations have been carried out for most of these new protocols.…”

Section: Introductionmentioning

confidence: 99%

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Chávez‐Rivera,

Navarro‐Santos,

Chacón‐García

et al. 2023

ChemistrySelect

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Strategies for introducing halogens and other inorganic groups in aromatic systems, usually involve non‐general and strong oxidative protocols which resulted in poor functional group compatibility. Iodine(III) reagents have emerged as an excellent alternative for the aromatic inorganic functionalization due to their low toxicity and strong oxidative character. In this context, the synergistic combination of different iodine(III) reagents and aluminum or ammonium salts including AlCl3, AlBr3, Al(NO3)3, NH4Cl, NH4Br and NH4I have recently demonstrated a great versatility for introducing the chlorine, bromine, iodine and nitro groups in aromatic systems, mainly phenols, anilines and some heterocycles. Using these common salts, their anions are softly oxidated by iodine(III) reagents, allowing the in situ formation of non‐described halogenating and nitrating species and in consequence, the introduction of these inorganic groups under an umpolung reactivity as chemical electrophilic synthons.

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Section: Introductionmentioning

confidence: 99%

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Chávez‐Rivera,

Navarro‐Santos,

Chacón‐García

et al. 2023

ChemistrySelect

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Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums

Garay‐Talero,

Acosta‐Guzmán,

Gamba‐Sánchez

2023

Adv Synth Catal

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This manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rings. Additionally, the utilization of chlorosulfonium salts as the chlorinating agent is demonstrated. The method emerges as an alternative to other processes where organic byproducts must be separated from the reaction mixture. In addition, the main byproducts are gaseous materials such as CO and CO2. This publication introduces the application of sulfoxides, oxalyl chloride, and aqueous hydrogen peroxide as the chlorination mixture.

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Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and Heterocyclic Scaffold Construction

de Mattos

2024

COC

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Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They are highly reactive, stable, easily handled, and have an excellent atom economy, transferring up to three halogen atoms to organic substrates. In these regards, the present review summarizes their synthetic applications as safe and convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, and heteroatoms, as well as radical halogenation involving saturated substrates and in situ halogenated intermediates for Appel-type reactions are presented and discussed. Remarkably, applications of trihaloisocyanuric acids in processes for the construction of heteroarene scaffolds based on electrophilic halo- and oxidative cyclization, multicomponent reactions, and telescopic reactions are also given.

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Chloroaromatics: Advances in Synthesis and Applications

Cited by 4 publications

References 99 publications

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums

Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and Heterocyclic Scaffold Construction

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