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Donor−Acceptor Assisted Alkyne Hydration: A Luminescent Boron-Stabilized Enol

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journal contribution
posted on 04.03.2011, 00:00 by Christina Sun, Jiasheng Lu, Suning Wang
An alkyne molecule 2-(2′-BMes2-phenylethynyl)pyridine (1) that contains a Lewis acidic BMes2 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′-BMes2-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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