Multigram scale cobalt catalyzed photochemical methoxycarbonylation of alkenes

Dragojlović, Veljko; Gao, Da Bin; Chow, Yuan L.

doi:10.1016/s1381-1169(01)00102-9

Cited by 14 publications

(7 citation statements)

References 26 publications

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“…In a typical example, irradiation of a metal complex leads to a coordinatively unsaturated species that has catalytic activity (as may have, for that matter, the ligand set free) . This is a convenient and often used method for the preparation of catalysts (also adsorbed on a solid − ), for example, for alkenes and alkynes di- or trimerization, rearrangement, metathesis , or CO insertion. − Since the catalyst is active thermally, the process proceeds further in the dark after the initial irradiation, whereas the reactions defined here as photocatalytic require that the irradiation is maintained. This type of process, thus, does not meet the definition proposed above and is not considered here.…”

Section: Introductionmentioning

confidence: 99%

Photocatalysis for the Formation of the C−C Bond

et al. 2007

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Section: Introductionmentioning

confidence: 99%

Photocatalysis for the Formation of the C−C Bond

et al. 2007

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“…15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system. 15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system.…”

Section: Discussionmentioning

confidence: 99%

“…Applications of a PTC technique in photochemistry are quite rare. 15-19,34, 35 Beugelmans et al 36,37 have reported an interesting synthetic example dealing with the photocyanation reactions of aromatic hydrocarbons with KCN and a crown ether or tetrabutylammonium cyanide in a water-dichloromethane system. We recently studied the effect of addition of an ammonium salt, serving as a surfactant, into the two-phase reaction system.…”

Section: Discussionmentioning

confidence: 99%

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

Klán

Ruzicka

Heger

et al. 2002

Photochem Photobiol Sci

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A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by a hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature in the region of -20 to 196 degrees C. The quantum yield of the 4-methoxyphenol formation was found to be temperature independent, in contrast to that of the 4-nitrophenol formation, suggesting that there is a temperature dependent process occurring after the partitioning between replacement of the nitro group and the methoxy group has taken place. The reaction was also investigated by using quantum chemical calculations. A technique for microwave-assisted photochemical synthesis is proposed as an efficient and practical tool for organic synthesis.

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“…After a long gap, in 2001, a Co-accelerated methoxycarbonylation reaction of alkene 11 under the irradiation of a mediumpressure Hg lamp (λ max = 310 nm) was reported by Dragojlovic et al (Scheme 5). 24 Notably, the reaction was also conducted successfully on a multigram scale (5−10 g) with a variety of alkenes. However, the authors found that the reaction was sensitive to steric crowding because sterically encumbered alkenes such as 1-methylcyclohexene, α-pinene, 5-vinyl-2norbornene, and Δ 3 -carene either did not react at all or provided a complex mixture of products.…”

Section: Alkoxy-and Hydroxycarbonylation (Synthesis Of Esters and Car...mentioning

confidence: 99%

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Singh

Sharma

2020

J. Org. Chem.

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In the last few decades, photocatalytic radical carbonylation strategies have received considerable attention as they are becoming a formidable tool in the toolbox of organic synthesis. These carbonylation strategies involve the incorporation of a carbon monoxide into organic molecules in an atom-and step-economical manner. Mostly, these strategies rely on the generation of an acyl radical as a key intermediate, which would be created via incorporation of CO molecule to an alkyl/aryl radical. The production of alkyl/aryl radical in these methodologies required either the high-intensity lightinduced transition-metal (TM)-catalyzed systems or visible-lightinduced photocatalytic systems that would be capable of mediating single electron transfer (SET) to the C(sp 3 )-or C(sp 2 )-hybridized coupling partners. Here, in this review, the development in the field of photocatalytic carbonylation is described by compiling the literature of the last 40 years, and their reaction mechanisms have been emphatically discussed. In addition, to aid readers, we have assimilated redox potentials of photocatalysts and substrates for a better sense of spontaneity of these photoredox carbonylation reactions.

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Multigram scale cobalt catalyzed photochemical methoxycarbonylation of alkenes

Cited by 14 publications

References 26 publications

Photocatalysis for the Formation of the C−C Bond

Photocatalysis for the Formation of the C−C Bond

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

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