Oxidation of Liquid Aldehydes by Molecular Oxygen.

McNesby, J. R.; Heller, Carl A.

doi:10.1021/cr60168a004

Cited by 119 publications

(73 citation statements)

References 19 publications

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“…[8] Additionally,t he exploration of new asymmetric catalytic methodologies of reactions where carbonyl compoundsa re used as starting materialsi ss tilli mportant for an efficient construction of interesting building blocks.C onsequently,t he development of Henry anda ldolr eactions starting from alcohols would open an ew area of researchi nt he progress of these interesting reactions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols

2017

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Pioneering aldol and Henry reactions starting from benzylic-type alcohols are described. The aldol reactionh as been successfully performed following ao ne-pot strategys tarting from alcohols, while the Henry reaction has been carried out following as equential protocol for the first time.I n both processes, enantiomerically enriched products were obtainedw ith good yields and high enantioselectivities.W eh ave also demonstrated that in reactions sensitive to small amounts of acid the use of alcohols instead of aldehydes could be ag ood solution for improving the results of these reactions.

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Section: Introductionmentioning

confidence: 99%

Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols

2017

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“…Indeed, the latter process has recently been used to prepare block copolymers.l 6 An electron transfer mechanism may obtain in the reduction of various organic compounds, such as aldehydes, 17 peroxides,l 8 and carbonium ions,l 9 by heavy metal cations, although in the first two cases a plausible group transfer mechanism can also be suggested. In each of these three reactions an organic free radical is produced; at least one of these systems serves as a redox catalyst for polymerization.…”

Section: Introductionmentioning

confidence: 99%

On the Theory of Oxidation-Reduction Reactions Involving Electron Transfer. III. Applications to Data on the Rates of Organic Redox Reactions

Marcus¹

1957

The Journal of Chemical Physics

263

133

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A recently developed theory of oxidation-reduction reactions (Part I) is used to calculate the rates of organic redox reactions whose mechanism involves the transfer of an electron from one reactant to the other. The theory can be used to discuss factors affecting the rates of these reactions. These factors include a standard free energy of reaction, the Coulombic interaction of the ionic charges of the reactants and the solvation of the charged reactants. Attention is focused on the relation between the rate of the redox ~tep in the over-ail process and the standard free energy change, AfiO, of this step, rather than on the more usual but less fundamental one between the corresponding quantities of the over-all process itself. . An approximate method is described for applying the theory to a molecule whose charge is not located at Its center. Essentially ail organic molecules lie in this category.As an example of these considerations, several typical reactions are discussed. These reactions involve the oxidation of a series of hydroquinones by ferric ions and of a series of leucoindophenols by dissolved oxygen. They ~re assun;.ed ~o possess electron transfer, rather than atom transfer, mechanisms. Free energies and entropies of activatiOn of the redox step are calculated using the theoretical equation. The calculated results are considered to be in reasonable agreement with the experimental data, no adjustable parameters being employed.

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“…Among these processes, photochemically generated singlet oxygen, 1 O 2 , can provide a clean and sustainable route to photo-oxidized compounds with high atom efficiency. This activation mode of oxygen relies on the use of organometallic complexes or organic dyes to absorb photons and to, subsequently, engage in energy transfer processes with 3 [24,25]. Thus, the oxidation of benzaldehyde by 1 O 2 using microreactors was evaluated.…”

Section: Resultsmentioning

confidence: 99%

“…On the lab-scale, the autoxidation of aldehydes has been catalyzed by numerous metallic ions in the form of salts, nanoparticles, or organic complexes [3,4]. However, we have shown that, due to low transfer rate of O 2 in the liquid phase, the chemical performances of aerobic oxidation (productivity and selectivity) can be falsified by oxygen starvation in the liquid phase [4,5].…”

Section: Introductionmentioning

confidence: 95%

Metal-Free, Visible Light-Promoted Aerobic Aldehydes Oxidation

Hamami¹,

Vanoye²,

Fongarland³

et al. 2016

J Flow Chem

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An efficient and metal-free method for the oxidation of aldehydes to the corresponding carboxylic acids has been developed. In a simple continuous-flow photochemical reactor, the use of camphorquinone (CQ) irradiated with a white light-emitting diode (LED) source enhanced the autoxidation of aldehydes. Under 5 bar of oxygen, visible light, and 0.3 mol% of CQ, the rate of oxidation was increased from 6 times with 2-ethylhexanal to 30 times for n-nonanal. The large interfacial area generated by a segmented flow apparatus associated with radicals formed by photooxidation of CQ ensures metal-free high throughput of carboxylic acids under safe conditions.

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Oxidation of Liquid Aldehydes by Molecular Oxygen.

Cited by 119 publications

References 19 publications

Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols

Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols

On the Theory of Oxidation-Reduction Reactions Involving Electron Transfer. III. Applications to Data on the Rates of Organic Redox Reactions

Metal-Free, Visible Light-Promoted Aerobic Aldehydes Oxidation

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