Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides: Recent Advances 2008–2021: Part I

Ajvazi, Njomza; Stavber, Stojan

doi:10.3390/compounds2010002

Cited by 15 publications

(22 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is known that a redox reaction between Selectfluor and iodide anion would readily occur to generate fluoride anion and molecular iodine (I 2 ) [13] . We therefore first wondered if the anti ‐Markovnikov Iodofluorination occurs via iodination by I 2 [14] . The I 2 /F − system was then used for the conversion of substrate 1 a (Scheme 4, eq 1).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

anti‐Markovnikov Iodofluorination of Alkenes

Qian

Zhang

Lin

et al. 2022

Chemistry An Asian Journal

View full text Add to dashboard Cite

The fluorination of alkenes with electrophilic N−F type reagents usually occurs through a Markovnikov‐type addition, and the anti‐Markovnikov‐type addition may require the use of a transition metal catalyst or an expensive catalyst. Herein we describe a convenient anti‐Markovnikov iodofluorination of alkenes with Selectfluor/nBu4NI. A wide substrate scope and good functional group tolerance were observed. The process allows for the construction of various C−F bonds, especially tertiary C−F bonds. The remarkable features make this protocol attractive, including convenient operations, simple reaction conditions, and the installation of an iodine atom which provides possibilities for further transformations.

show abstract

Section: Resultsmentioning

confidence: 99%

“…[13] We therefore first wondered if the anti-Markovnikov Iodofluorination occurs via iodination by I 2 . [14] The I 2 /F À system was then used for the conversion of substrate 1 a (Scheme 4, eq 1). Low yields were obtained (2% ~13%), no matter which fluoride source was used, reflecting that the I 2 /F À path can be ignored.…”

Section: Resultsmentioning

confidence: 99%

anti‐Markovnikov Iodofluorination of Alkenes

Qian

Zhang

Lin

et al. 2022

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…As an important branch in the field of electrophilic halogenation, electrophilic iodofunctionalization of alkenes has attracted special attention in the past decades because it possesses unique synthetic advantages. − On the one hand, this powerful transformation offers direct access to iodine-functionalized molecules by simultaneously incorporating iodine and another functional group into the double bond of the parent alkenes under mild conditions. It is known that iodine-containing molecules are of great importance because not only their structural moieties are present in bioactive molecules such as marine natural products (Scheme a) but also they can be manipulated very easily.…”

Section: Introductionmentioning

confidence: 99%

“…The easy manipulation makes them a good platform for the synthesis of a wide range of valuable complicated compounds . On the other hand, this reaction triggered by electrophilic iodine provides a possibility for the transformations of challenging substrates into the desired compounds, which cannot be reached via reactions promoted by other types of electrophilic reagents because of the distinction of the reactivities of electrophilic iodine and the formed iodiranium ion intermediates . Despite the advantages, not many methods are available for catalytic asymmetric transformations in this field.…”

Section: Introductionmentioning

confidence: 99%

“…The obtained products could be easily transformed into various valuable chiral molecules such as α-aryl ketones, chiral secondary amines, and aziridines. This work represents the first example of organocatalytic enantioselective intermolecular iodinative difunctionalization of alkenes , and provides a convenient route for modular entry to iodine-functionalized chiral molecules. Importantly, it also exhibits the unique nature of electrophilic iodine-promoted transformation of alkenes and the advantages of the control of electrophilic iodine by chiral sulfide, which offer a basis for the design of new iodination reactions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric Intermolecular Iodinative Difunctionalization of Allylic Sulfonamides Enabled by Organosulfide Catalysis: Modular Entry to Iodinated Chiral Molecules

Liao

et al. 2022

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Electrophilic halogenation of alkenes is a powerful transformation offering a convenient route for the construction of valuable functionalized molecules. However, as a highly important reaction in this field, catalytic asymmetric intermolecular iodinative difunctionalization remains a formidable challenge. Herein, we report that an efficient Lewis basic chiral sulfide-catalyzed approach enables this reaction. By this approach, challenging substrates such as γ,γdisubstituted allylic sulfonamides and 1,1-disubstituted alkenes with an allylic sulfonamide unit undergo electrophilic iodinative difunctionalization to give a variety of iodine-functionalized chiral molecules in good yields with excellent enantio-and diastereoselectivities. A series of free phenols as nucleophiles are successfully incorporated into the substrates. Aside from phenols, primary and secondary alcohols, fluoride, and azide also serve as efficient nucleophiles. The obtained iodinated products are a good platform molecule, which can be easily transformed into various chiral compounds such as α-aryl ketones, chiral secondary amines, and aziridines via rearrangement or substitution. Mechanistic studies revealed that the chiral sulfide catalyst displays a superior effect on control of the reactivity of electrophilic iodine and the enantioselective construction of the chiral iodiranium ion intermediate and catalyst aggregates might be formed as a resting state in the reactions.

show abstract

Accessing Borazine Substitution Patterns through Late‐Stage Iodination

Marchionni,

Nazari Khodadadi,

Cela

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

We have defined a procedure for the late‐stage functionalization of aryl borazines to facilitate the synthesis of a diverse array of borazine derivatives with varying substitution patterns, paving the way for further exploration of the field. More in detail, we have studied and disclosed a simple iodination procedure that could be applied to several differently substituted substrates (1 a–i) with mostly good to excellent yields (47–96%). The representative iodinated compounds 2 b and 2 e, were utilized to test their use in further representative functionalization steps such as cyanation, Heck, and Sonogashira reactions. All products 3 a–e were obtained in satisfactory good to very good yields considering the multiple (three or six times) concomitant reactions.

show abstract

Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides: Recent Advances 2008–2021: Part I

Cited by 15 publications

References 67 publications

anti‐Markovnikov Iodofluorination of Alkenes

anti‐Markovnikov Iodofluorination of Alkenes

Asymmetric Intermolecular Iodinative Difunctionalization of Allylic Sulfonamides Enabled by Organosulfide Catalysis: Modular Entry to Iodinated Chiral Molecules

Accessing Borazine Substitution Patterns through Late‐Stage Iodination

Contact Info

Product

Resources

About