Related Experiment Video
Updated: Aug 16, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Synthesis of Benzylic Alcohols by Decarboxylative Hydroxylation
Qian Yu1, Donglin Zhou1, Yaoyue Liu1
1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
Abstract:
Herein, we demonstrate an efficient method for the decarboxylative hydroxylation of carboxylic acids with silver(I) as the catalyst and cerium ammonium nitrate as the oxidant and its utility in chemoselective late-stage functionalization of natural products and drug molecules. The chemoselectivity of this protocol arises from a benzylic nitrate intermediate that retards further oxidation and is hydrolyzed to the final benzylic alcohol product. Mechanistic investigation reveals that the facile oxidation of silver carboxylate affords silver(II) species as an intermediate oxidant responsible for decarboxylation.
Related Concept Videos
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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.
Hydroboration-Oxidation of Alkenes
Acid-Catalyzed Dehydration of Alcohols to Alkenes

