Aromatic Halogenation

Abstract

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Selective Oxidation of Clopidogrel by Peroxymonosulfate (PMS) and Sodium Halide (NaX) System: An NMR Study

“…The direct insertion of halogens in (hetero)aromatic drugs, in a selective way, has been the object of much interest by the synthetic community [ 1 ]. The inclusion of a new C−X bond in these bioactive heterocyclic compounds can improve their physical and biological properties, increase potency, and be used as a handle in the further design and construction of pharmaceuticals [ 2 ].…”

“…In recent years, several methods of direct activation of halogens in organic compounds have been reported using safe halogen sources such as HX, NH 4 X and NaX (X = Cl, Br and I). To sustainably transform these halides into more reactive species, the use of oxidizing agents that conform to the principles of Green Chemistry is essential [ 1 ].…”

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

“…The direct halogenation of aromatic compounds is one of the most fundamental and frequently used reactions in organic chemistry because the halide functionalities offer numerous possible transformations afterward. , Furthermore, the remarkable development of transition-metal-catalyzed coupling techniques has greatly reinforced their synthetic value over the past decades. , Halogen functionalities can widely modulate the electronic, lipophilic, and steric properties of the attached frameworks. It thus can be appreciated that the haloarenes fulfill a dichotomous function in many research fields involving pharmaceuticals, agrochemicals, material science, and imaging technics.…”

Transition-Metal-Free Site-Selective γ-C(sp2)–H Monoiodination of Arenes Directed by an Aliphatic Keto Group

“…Actually, there are some synthetic challenges in this expected transformation. (1) The suppression of iodination at the highly activated benzylic position, and/or the α′-position of the carbonyl group needs to be solved; − (2) the competition of monoiodination at para - or ortho -positions is a well-known phenomenon, especially for a substrate bearing a sterically hindered cyclohexanone substituent at the aryl ring; (3) suppression of undesired ortho - and para -position bisiodination; and (4) other competitive noniodination reactions may also occur under the oxidative reaction conditions . After numerous reaction media were tested, fortunately, the expected monoiodination product 2a was isolated in 87% yield when the reaction was performed in hexafluoroisopropanol (HFIP), while 14% and 11% NMR yields were obtained in CH 3 NO 2 and CF 3 CH 2 OH, respectively (entries 1–3, Table ).…”