Abstract
The carbon–carbon double bond, with its diverse and multifaceted reactivity, occupies a prominent position in organic synthesis. Although a variety of simple alkenes are readily available, the mild and chemoselective introduction of a unit of unsaturation into a functionalized organic molecule remains an ongoing area of research, and the olefination of carbonyl compounds is a cornerstone of such approaches. Here we show the direct olefination of hydrazones via the intermediacy of three-membered ring species generated by addition of sulfoxonium ylides, departing from the general dogma of alkenes synthesis from carbonyls. Moreover, the mild reaction conditions and operational simplicity of the transformation render the methodology appealing from a practical point of view.
Highlights
The carbon–carbon double bond, with its diverse and multifaceted reactivity, occupies a prominent position in organic synthesis
Some of the most powerful reactions available to organic chemists rely on the reactivity of olefins: the Heck reaction, olefin metathesis and the Sharpless asymmetric dihydroxylation are notable examples[2,3,4], coincidentally all recognized by Nobel Prizes during the last 16 years
There are a number of different possible approaches for the introduction of a double bond into a molecule, amongst which the olefination of carbonyl moieties is the most developed[5, 6]
Summary
The carbon–carbon double bond, with its diverse and multifaceted reactivity, occupies a prominent position in organic synthesis. We proposed the transient generation of an N-iminyl aziridine and its subsequent cheletropic cycloreversion[23,24,25,26,27,28] to unveil the desired olefin product. The formation of an N-iminyl aziridine from a carbonyl precursor in a synthetically useful manner[29, 30] and finding appropriate conditions for a facile cheletropic elimination[31].
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