An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

“…[135] In addition, a number of protocols make use of IBX to directly oxidize alcohol intermediates generated in the course of the reaction. [136,137] For example, a combination of IBX and I 2 /H 2 O can be used for the direct transformation of alkenes into 2iodoketones without isolation of the initially formed halohydrins. [137] Fanciful applications of this simple principle appear to have no limits.…”

“…[136,137] For example, a combination of IBX and I 2 /H 2 O can be used for the direct transformation of alkenes into 2iodoketones without isolation of the initially formed halohydrins. [137] Fanciful applications of this simple principle appear to have no limits. A method developed by Werz and co-workers exploits a ring expansion reaction for the anti-selective synthesis of oligoacetals.…”

Gold‐Catalyzed Cycloisomerization–Halogenation Sequence of 1,3‐Enyne Esters with NXS: Efficient Synthesis of 5‐Bromo/Iodo Cyclopentenones

“…α‐Halo carbonyl compounds such as α‐Brominated and α‐iodinated ketones are not only the core structure moieties existing in biologically natural products and pharmaceuticals, but also serve as the versatile synthetic precursors for the preparation of a wide variety of highly complex molecules, Thus, the development of efficient protocols for the regioselective synthesis of this privileged scaffolds has received increasing attention and numerous methods have been established . By far the most prevalent and straightforward strategies for preparing α‐Bromo and α‐iodo ketones are rely on the halogenation of ketones with molecular bromine or N‐bromosuccinimide (NBS)/N‐iodosuccinimide (NIS) in the presence of Lewis or protic acids.…”

“…Due to the toxic and hazardous nature of bromine, the combination bromide/iodide salts with a suitable oxidant has emerged as an alternative protocol . Apart from these methods, a variety of synthetic strategies from different class of feedstocks have been realized, including transition‐metals or acid catalyzed hydration of haloalkynes, oxidation of vinyl halides or olefins, direct conversion of alcohols, dearomative halogenation of phenols, and other processes . While remarkable progress has been achieved, current reported methods were still limited to acyclic α‐bromo/iodo ketones, and the synthesis of cyclic enones with a X (Br, I)‐containing all‐substituted stereocenter from readily available acyclic precursors are particularly scarce …”

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

“…, um alkoholische Intermediate direkt weiter zu oxidieren [136,137]. So können beispielsweise Alkene durch die Kombination von IBX mit I 2 /H 2 O ohne Isolierung Schema 14.…”