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Updated: Oct 11, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
Jie Li1, Pei Zhao1, Ruoling Li1
1State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.
Abstract:
An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile carbon-boron bond transformations, were readily converted into diverse synthetically useful molecules, including α-hydroxy ketones, functionalized SEEs, and gem-difunctionalized aldehydes.
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