2011
DOI: 10.1002/chin.201113253
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ChemInform Abstract: Direct Nuclear Halogenation of Deactivated Aryl and N‐Heteroaryl Amines

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Cited by 3 publications
(4 citation statements)
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“…Figure 7 shows the effect of reaction time for benzoylation of toluene carried out over a period of 3 h. The reaction resulted in 65% conversion at 0.5 h and increased to 100% conversion at 1 h. The selectivity for the para-product (4-MBP) decreased as the time increased. It is known that in non-polar solvents (in this case toluene), the ortho-product is favored [29]. However, in our study, it is interesting to observe that the selectivity for 2-MBP increased with time.…”
Section: Effect Of Reaction Timementioning
confidence: 43%
“…Figure 7 shows the effect of reaction time for benzoylation of toluene carried out over a period of 3 h. The reaction resulted in 65% conversion at 0.5 h and increased to 100% conversion at 1 h. The selectivity for the para-product (4-MBP) decreased as the time increased. It is known that in non-polar solvents (in this case toluene), the ortho-product is favored [29]. However, in our study, it is interesting to observe that the selectivity for 2-MBP increased with time.…”
Section: Effect Of Reaction Timementioning
confidence: 43%
“…Direct iodination using I 2 is a simple method, but is not straight forward and requires the oxidation of iodine to the more reactive species with a pronounced I + nature. 25 Iodination using ICl is carried out in Lewis acids 26 such as Hg(OTf) 2 and AgOTf. 6 Several reagents reported for iodination of aromatic compounds include iodine and 1,4bis(triphenylphosphonium)-2-butene peroxodisulfate 7 , iodine and pyridine/dioxane 8 , AgNO 3 /I 2 9 , I 2 /NaBO 3 .4H 2 O in ionic liquid 10 , I 2 /HIO 3 , heat 11 , I 2 /CrO 3 13 , NaClO 2 /NaI/HCl 14 , KI/K 2 FeO 4 in water 15 , N-iodosuccinimide and catalytic trifluoroacetic acid 16 , pyCl/CH 3 OH 17 , I 2 /Pb(OAc) 4 12 , KI/H 2 O 2 18 , KI/KIO 3 /H +19 , KClO 3 /KI/HCl 20 , NCS/NaI 21 and iodine with H 2 O 2 and O 2 .…”
Section: Introductionmentioning
confidence: 99%
“…hydrochloric acid, sulphuric acid, etc., in which the heterolytic dissociation facilitates electrophilic attack of iodine. 25 Iodination using ICl is carried out in Lewis acids 26 such as Hg(OTf) 2 and AgOTf.…”
Section: Introductionmentioning
confidence: 99%
“…µειώνεται καθώς αυξάνεται ο όγκος τους (όγκος: Ι>Br>Cl, δραστικότητα: Cl >Br>I).Αντίθετα, η εκλεκτικότητα της εισαγωγής αλογονοατόµου (σχηµατισµός του 5αλογονωµένου προϊόντος αποκλειστικά) στον δακτύλιο αυξάνεται καθώς αυξάνεται ο όγκος του ατόµου αλογόνου (όγκος: Ι>Br>Cl, εκλεκτικότητα: Ι>Br>Cl).Επίσης, έχει παρατηρηθεί ότι η αλογόνωση ιµιδαζολίων µε την χρήση Ν-αλογονοηλεκτριµιδίων ευνοείται σε πολικούς διαλύτες (CH 3 CN, THF, DMF κ.α. ), επειδή σε αυτούς τα Ν-αλογονο-ηλεκτριµίδια καθίστανται δραστικότερα [461]. Η προσθήκη ατόµου αλογόνου στην 5-θέση ενός ιµιδαζολίου πραγµατοποιείται, όπως απόσπαση του πρωτονίου αυτού γίνεται παρουσία βάσης: το αρνητικά φορτισµένο κατάλοιπο του Ν-αλογονο-ηλεκτριµιδίου λειτουργεί ως ισχυρή βάση και δεσµεύει το πρωτόνιο αυτό.Σχήµα Γ.4.2.1.3: Συγκριτικά NMR φάσµατα σε CDCl 3 (Α) της ένωσης 59 και (Β) του χλωριωµένου παραγώγου της, 70, στα οποία υποδεικνύεται το σηµείο εισαγωγής του ατόµου χλωρίου (ιµιδαζολική 5-θέση).…”
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