Oxidative selenofunctionalization of allenes: convenient access to 2-(phenylselanyl)-but-2-enals and 4-oxo-3-(phenylselanyl)pent-2-enoates‡

文献情報

出版日 2019-05-24

DOI 10.1039/C9QO00561G

インパクトファクター 5.281

著者

Benito Alcaide, Pedro Almendros, Teresa Martínez del Campo, Laura Martín, Guillermo Palop, Mireia Toledano-Pinedo

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要旨

The controlled preparation of two types of α-seleno-α,β-unsaturated carbonyls, namely, α-selenoenals and α-selenoenones, has been accomplished directly from allenes through metal-free oxidative selenofunctionalization reactions. The decisive role of organoselenium and 1-fluoropyridinium reagents has been disclosed. The divergent reactivity due to the presence or absence of an ethoxycarbonyl moiety at the allene end has also been studied. A tentative pathway implying selective electrophilic addition of the selenium reagent to the allene moiety followed by adventitious water attack and concomitant oxidation has been proposed.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Oxidative selenofunctionalization of allenes: convenient access to 2-(phenylselanyl)-but-2-enals and 4-oxo-3-(phenylselanyl)pent-2-enoates‡

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