Oxidative selenofunctionalization of allenes: convenient access to 2-(phenylselanyl)-but-2-enals and 4-oxo-3-(phenylselanyl)pent-2-enoates12. Issue 14 (31st May 2019)

• Record Type: Journal Article
• Authors: Alcaide, Benito; Almendros, Pedro; Martínez del Campo, Teresa; Martín, Laura; Palop, Guillermo; Toledano-Pinedo, Mireia
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 14(2019)
• Page Start: 2447
• Page End: 2451
• Publication Date: 2019-05-31
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00561g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The controlled preparation of two types of α-seleno-α, β-unsaturated carbonyls, namely, α-selenoenals and α-selenoenones, have been accomplished. Abstract : 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.