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Updated: Jan 6, 2026
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic Hydroboration of Aldehydes, Ketones, and Alkenes Using Potassium Carbonate: A Small Key to Big
Da Hun Ma1, Ashok Kumar Jaladi1, Ji Hye Lee1
1Department of Chemistry, Kangwon National University, Chuncheon 24341, Republic of Korea.
Abstract:
An efficient transition-metal-free protocol for the hydroboration of aldehydes and ketones (reduction) was developed. The hydroboration of a wide range of aldehydes and ketones with pinacolborane (HBpin) under the K2CO3 catalyst has been studied. The reaction system is practical and reliable and proceeds under extremely mild and operationally simple conditions. No prior preparation of the complex metal catalyst was required, and hydroboration occurred stoichiometrically. Further, the chemoselective reduction of aldehydes over ketones was carried out. Moreover, we demonstrated the use of K2CO3 as an efficient catalyst for the hydroboration of alkenes. The operational simplicity, inexpensive and transition-metal-free catalyst, and the applicability to gram-scale synthesis strengthen its potential applications for hydroboration (reduction) at an industrial scale.
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02:47Alkynes 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.
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02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
01:33Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.