IBX/I2-mediated oxidation of alkenes and alkynes in water: a facile synthesis of α-iodoketones

Yadav, J. S.; Reddy, B. V. Subba; Singh, Ashutosh Pratap; Basak, A. K.

doi:10.1016/j.tetlet.2008.07.120

Cited by 41 publications

(12 citation statements)

References 35 publications

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“…Thes uccess of the above oxidative fluorination of vinyl MIDAb oronates encouraged us to explore the feasibility of other halogenation reactions. [13,15] Gratifyingly,t he reaction was also amenable for the formation of chlorinated, [25] brominated, [26] and iodinated [25] a-boryl ketones using NaClO 2 ,N BS,a nd I 2 as the halogen sources,r espectively (Scheme 1). [13,15] In general, moderate to good yields were obtained and decent functional group tolerance was observed.…”

Section: Communicationsmentioning

confidence: 99%

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α‐Boryl Ketones

Zeng

et al. 2016

Angew Chem Int Ed

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The synthesis of halogenated and trifluoromethylated α-boryl ketones via a one-pot oxidative difunctionalization of alkenyl MIDA boronates is reported. These novel densely functionalized organoborons bearing synthetically and functionally valuable carbonyl, halogen/CF3 and boronate moieties within the same molecule are synthetically challenging for the chemist, but have great synthetic potential, as demonstrated by their applications in a straightforward synthesis of borylated furans. The generality of this reaction was extensively investigated. This reaction is attractive since the starting materials, alkenyl MIDA boronates, are easily accessible.

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Section: Communicationsmentioning

confidence: 99%

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α‐Boryl Ketones

Zeng

et al. 2016

Angew Chem Int Ed

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“…Similarly to the alkene systems mentioned above, I 2 - and IBX-based oxyiodination of aromatics was also applied to alkynes in water ( Scheme 60 ) [ 155 ]. The protocol showed good tolerance towards electron-donating and electron-withdrawing substitutions on the aromatic alkynes.…”

Section: Oxyhalogenation Of Hydrocarbonsmentioning

confidence: 99%

Synthetic Access to Aromatic α-Haloketones

et al. 2022

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α-Haloketones play an essential role in the synthesis of complex N-, S-, O-heterocycles; of which some exhibit a remarkable biological activity. Research further illustrated that α-bromo-, α-chloro-, and α-iodoketones are key precursors for blockbuster pharmacological compounds. Over the past twenty years, substantial advances have been made in the synthesis of these industrially relevant building blocks. Efforts have focused on rendering the synthetic protocols greener, more effective and versatile. In this survey, we summarised and thoroughly evaluated the progress of the field, established in the past two decades, in terms of generality, efficacy and sustainability.

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“…Along with linear alkenes, cyclic and heterocyclic alkenes were found to proceed smoothly to the corresponding iodoketones 56 at room temperature. In addition, terminal aryl alkynes were also able to be transformed into iodoketones 55 under standard conditions (Scheme ) …”

Section: Carbonyl Formation By Oxygenation Based On Partial Cleavagementioning

confidence: 99%

Recent Advances in Transition‐Metal‐Free Oxygenation of Alkene C=C Double Bonds for Carbonyl Generation

Wan

Gao

2016

Chemistry An Asian Journal

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Carbonyl-forming reactions are a class of fundamental transformations in organic chemistry. Guided by the current importance of environmentally benign metal-free catalysis and synthesis, herein we review recent advances in carbonyl-generation reactions based on alkene C=C double oxygenation as well as related cascade reactions in the synthesis of diverse organic products. The content of this focus review consists of two important but different reaction models: oxygenation based on full C=C double-bond cleavage and oxygenation based on partial C=C double-bond cleavage.

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IBX/I2-mediated oxidation of alkenes and alkynes in water: a facile synthesis of α-iodoketones

Cited by 41 publications

References 35 publications

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α‐Boryl Ketones

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α‐Boryl Ketones

Synthetic Access to Aromatic α-Haloketones

Recent Advances in Transition‐Metal‐Free Oxygenation of Alkene C=C Double Bonds for Carbonyl Generation

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