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Updated: Jun 4, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Donor-acceptor assisted alkyne hydration: a luminescent boron-stabilized enol
Christina Sun1, Jiasheng Lu, Suning Wang
1Department of Chemistry, Queen's University, Kingston, Ontario, Canada.
Abstract:
An alkyne molecule 2-(2'-BMes(2)-phenylethynyl)pyridine (1) that contains a Lewis acidic BMes(2) group and a Lewis basic pyridyl group has been found to undergo facile hydration under ambient conditions in the presence of CuI, forming a highly emissive and stable enol ester (2). The lack of any hydration reactivity by a control compound 2-(2'-BMes(2)-phenylethynyl)benzene (3) under the same conditions supports that the cooperativity between the Lewis donor and acceptor groups plays a key role in the formation of 2.
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