Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones
Dipali A Chaudhari1, Rodney A Fernandes1
1Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, Maharashtra, India.
Abstract:
A mimic of the Wacker process for C═O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.
Related Concept Videos
Oxidation of Alcohols
The process of oxidation in a chemical reaction is observed in any of the three forms:
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Multiple Halogenation of Methyl Ketones: Haloform Reaction
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.


