1,3-Oxa/Thia-2-Azoles

Howard, J. K.

doi:10.1016/b978-0-12-818655-8.00048-2

Cited by 1 publication

(1 citation statement)

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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%