2019
DOI: 10.1021/acs.orglett.9b02569
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Catalyst-Free Selective Oxidation of Diverse Olefins to Carbonyls in High Yield Enabled by Light under Mild Conditions

Abstract: The selective oxidation of olefins, in particular, aromatic olefins to carbonyls, is of significance in organic synthesis. In general, stoichiometric toxic oxidants or a highcost catalyst is required. Herein we report a novel and practical light-enabled protocol for the synthesis of carbonlys in high yield through a catalyst-free oxidation of olefins using H 2 O 2 as a clean oxidant. A broad scope of carbonyls can be synthesized in high yield, and no catalyst or toxic oxidant is required.

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Cited by 30 publications
(9 citation statements)
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“…Successively, the generated intermediate is attached by the peroxy oxygen and formed di‐hydroxyl intermediate XV . In the end, the aldehyde XVI was formed by the decomposition of di‐hydroxyl intermediate XV (Figure 2, C ) [39] . Based on previously reported studies and obtained results, we hypothesized the plausible mechanistic pathway for the selective oxygenation reactions (Figure 2, A – C ).…”
Section: Resultsmentioning
confidence: 57%
“…Successively, the generated intermediate is attached by the peroxy oxygen and formed di‐hydroxyl intermediate XV . In the end, the aldehyde XVI was formed by the decomposition of di‐hydroxyl intermediate XV (Figure 2, C ) [39] . Based on previously reported studies and obtained results, we hypothesized the plausible mechanistic pathway for the selective oxygenation reactions (Figure 2, A – C ).…”
Section: Resultsmentioning
confidence: 57%
“…Oxidation of organic alkenes resulting in C=C bond cleavage and formation of a carbonyl moiety using O 2 as an oxidant is generally achieved either photo‐ [30] or thermo‐catalytically [31] . Alkene oxidation under catalyst free conditions is currently of interest in organic chemistry, [32] with the formation of 3 c an unanticipated example of such a process.…”
Section: Resultsmentioning
confidence: 99%
“…Polycyclic aromatic hydrocarbon α ‐Methyl naphthalene ethylene ( 24 ) was also oxidated to the corresponding ketones in mild yield. In 2019, Zhao's team used H 2 O 2 as an oxidant to oxidize olefins to aldehydes or ketones under photocatalytic conditions [17] . Liu′s team in 2021 reported an oxidation cracking reaction of aromatic olefins at high temperatures [16] .…”
Section: Methodsmentioning
confidence: 99%