Pd/Cu-catalyzed oxidation of alkynes into 1,2-diketones using DMSO as the oxidant

Gao, Ang; Yang, Fan; Ji, Li; Wu, Yangjie

doi:10.1016/j.tet.2012.04.069

Cited by 87 publications

(35 citation statements)

References 38 publications

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“…169 Other procedures that combine DMSO and molecular oxygen as dual oxidants using 10% Pd/C (10 mol%) as catalyst can be used, as shown in the typical formation of benzil (159) from diphenylacetylene (Scheme 59). 170 It is necessary to note that all these DMSO-containing oxidation procedures produce unpleasant dimethylsulfide as oxidation residue.…”

Section: 2-diketonesmentioning

confidence: 99%

Chemicals from Alkynes with Palladium Catalysts

2013

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Section: 2-diketonesmentioning

confidence: 99%

Chemicals from Alkynes with Palladium Catalysts

2013

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“…The Pd/Cu-catalyzed oxidation reaction of 5 gives the 1,2-di(thiophen-3-yl)ethane-1,2-dione 4 in 90% yield. 59 Derivative 4 can be even more conveniently prepared in two steps, starting from commercially available aldehyde 8 . The N -heterocyclic carbene-catalyzed benzoin condensation of 8 affords the alcohol 7 in excellent yield and under very mild conditions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Dithienocyclohexanones (DTCHs) as a Family of Building Blocks for π-Conjugated Compounds in Organic Electronics

et al. 2017

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The development and widespread application of organic electronic devices require the availability of simple and cost-effective suitable materials. In this study, the preparation of a new class of conjugated compounds on the basis of a dithienocyclohexanone (DTCH) core is reported. Several synthetic strategies for the preparation of dialkyl DTCH derivatives are explored, with special emphasis on the establishment of a sustainable synthetic access. Two successful synthetic pathways, both consisting of five steps, are identified: the first one featuring readily available 3-thiophenecarboxaldeyde and the second one 3-ethynylthiophene as the starting materials. Both procedures are characterized by reasonably high overall yields (over 30%) and remarkably low E factors (<400). Preliminary evidences of the use of such building blocks in the micellar Suzuki–Miyaura cross-coupling reactions leading to promising molecular semiconductors are also given. Moreover, on a small molecule containing DTCH moiety, solar cell performance was investigated.

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“…Variety of synthetic methods for 1,2‐diketones are known, for instances C−H oxidation of 1,2‐diarylalkenes, oxidation of 1,2‐diarylalkynes, oxidation of benzoins, oxidation of deoxybenzoins, oxidation of hydrobenzoins, cleavage of 1,3‐diketones, cleavage of α,β‐unsaturated ketones, etc. Most of the mentioned methods used toxic and expensive catalysts or oxidants.…”

Section: Figurementioning

confidence: 99%

Oxidative Coupling of Naphthols to Ketones: An Approach to 1,2‐Diketones

et al. 2018

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1,2‐Diketones are highly useful building blocks for the synthesis of pharmaceuticals, natural products and heterocycles. A simple and efficient route to 1,2‐diketones is developed here. The strategy involves coupling of naphthols to methyl ketones via oxidative C−H functionalization of methyl group of ketones. CuI (10 mol %) is used as catalyst and FeSO4.7H2O (10 mol %) as additive, both of which are environmentally benign and cheap. The reaction is carried out in DMSO solvent at 120 oC for 8–10 h. Little amount of 1,1′‐bi‐2‐naphthol (BINOL) is also formed as side product. A tentative mechanism is proposed for the reaction which demonstrates a free‐radical pathway. Although Cu(I) is used as catalyst, however, the in situ generated Cu(II) behaves as the active catalytic species. Aerial oxygen acts as the oxygen source for the newly formed carbonyl functional group.

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Pd/Cu-catalyzed oxidation of alkynes into 1,2-diketones using DMSO as the oxidant

Cited by 87 publications

References 38 publications

Chemicals from Alkynes with Palladium Catalysts

Chemicals from Alkynes with Palladium Catalysts

Synthesis of Dithienocyclohexanones (DTCHs) as a Family of Building Blocks for π-Conjugated Compounds in Organic Electronics

Oxidative Coupling of Naphthols to Ketones: An Approach to 1,2‐Diketones

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