One-pot enol silane formation-alkylation reactions of ketones promoted by trimethylsilyl trifluoromethanesulfonate: Direct access to β,β-diarylated ketones and related compounds

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-05-28 DOI:10.1016/j.tetlet.2025.155679

Katelyn A. Marchione, Karmen M. Smith, C. Wade Downey

引用次数: 0

Abstract

Ketones undergo enol silane formation and subsequent alkylation in a single reaction flask when treated with an amine base, a secondary alkyl acetate, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The reaction appears to be general to a wide range of alkyl and aryl ketones as well as ester, thioester, amide, and aldehyde pronucleophiles. Diarylmethyl acetates are ideal electrophiles, as are certain monoarylmethyl acetates, undergoing ionization to form secondary carbocations in the presence of TMSOTf. These reactions occur under mild conditions with exceptional efficiency, including 15 examples over 90 % yield.

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一锅烯醇硅烷生成-三甲基硅基三氟甲烷磺酸促进酮类的烷基化反应：直接获得β、β-二芳化酮类及相关化合物

酮经过烯醇硅烷形成和随后的烷基化在一个单一的反应烧瓶中，当处理与胺碱，仲烷基乙酸酯和三甲基硅基三氟甲烷磺酸（TMSOTf）。该反应似乎适用于广泛的烷基和芳基酮以及酯、硫酯、酰胺和醛亲核试剂。二芳基乙酸甲酯是理想的亲电试剂，某些单芳基乙酸甲酯也是如此，在TMSOTf存在下电离形成仲碳正离子。这些反应在温和的条件下发生，效率很高，其中有15个反应的产率超过90%。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.