One-Pot Formylation and Dimerization of p-Alkyl Phenols Using DCMT-Activated DMSO

Chu, Guobiao; Zhang, Yu; Gao, Feng; Li, Chunbao

doi:10.1080/00397911.2011.590916

Cited by 15 publications

(12 citation statements)

References 14 publications

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“…On the basis of all of the results described above together with previous literature, 15,39,40,51,52 especially several papers concerning the variant of the Pummerer reaction, 13,15,53 a possible mechanism of this transformation is proposed in Scheme 2. The reaction starts from a single electron-transfer The Journal of Organic Chemistry oxidation of 2,3-dihydro-1H-pyrroles 1 by Fe 3+ and O 2 in air to generate radical species A.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

“…1 H NMR (400 MHz, DMSO-d 6 ) δ 10.00 (s, 1H), 9.33 (s, 1H), 7.83 (s, 1H), 7.80 (d, J = 8.8 Hz, 2H), 7.47 (t, J = 8.0 Hz, 1H), 7.38 (d, J = 8.8 Hz, 2H), 7.13 (dd, J = 8.0, 2.0 Hz, 1H), 7.02 (t, J = 2.0 Hz, 1H), 6.97 (d, J = 7.6 Hz, 1H), 3.81 (s, 3H), 2.34 (s, 3H). 13 N-(4-Chlorophenyl)-5-formyl-1-(2-methoxyphenyl)-2-methyl-1H-pyrrole-3-carboxamide (2j). The product was isolated by flash chromatography (eluent ethyl acetate/petroleum ether = 1:3) as a white solid (199 mg, 54%).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…12 Formylation and dimerization of p-alkyl-substituted phenols also has been achieved by Yu's group in 2012 by using DCMT-activated DMSO. 13 Very recently, several valuable reactions that avoided the use of too harsh one-carbon donors (such as the Vilsmeier−Haack reagent) have been achieved by using DMSO as a one-carbon source in the presence of transition metal catalysts. Cheng's group developed an NH 4 OAcpromoted C3-formylation of indoles under nearly neutral conditions with DMSO serving as a carbonyl reagent.…”

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Dimethyl Sulfoxide Participant Iron-Mediated Cascade Oxidation/α-Formylation Reaction of Substituted 2,3-Dihydropyrroles under Air and Protonic Acid Free Condition

et al. 2014

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An efficient and Brønsted acid free one-pot protocol to directly generate structurally sophisticated α-formylpyrrole derivatives in moderate to good yields has been demonstrated, involving an iron-mediated domino oxidation/formylation reaction of readily available 2,3-dihydro-1H-pyrroles in dimethyl sulfoxide and air atmosphere, in which dimethyl sulfoxide acts as the formyl donor. A possible mechanism is presented.

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Section: ■ Results and Discussionmentioning

confidence: 93%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Dimethyl Sulfoxide Participant Iron-Mediated Cascade Oxidation/α-Formylation Reaction of Substituted 2,3-Dihydropyrroles under Air and Protonic Acid Free Condition

et al. 2014

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“…Three other reports of C-H formylation and related transformations of aromatic substrates have been published by the research groups of Yu, 66 Chiba, 67 and Suzuki. 68 Mechanistic rationale:…”

Section: Review Syn Thesismentioning

confidence: 99%

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

2016

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Dimethyl sulfoxide is generally characterized as a solvent and oxidant rather than as a substrate, building block, or synthon in organic chemistry. However, an abundance of reports have recently appeared that demonstrate dimethyl sulfoxide acting in these roles. This review article offers a comprehensive summary of the literature on this topic until the end of 2015. Synthetic transformations that have utilized the 'C-S-C', 'C', and 'C-S' fragments of dimethyl sulfoxide as building blocks are systematically summarized. 1 Introduction 2 History and Recent Highlights of DMSO-Based Oxidations 3 DMSO-Based Methylthiomethylation (-CH 2 SMe) 4 DMSO as a One-Carbon Synthon 4.

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“…DMSO serves as a source of a wide range of functional groups in organic reactions, such as −O, −SMe, −CH 2 SMe, −SO 2 Me, −Me, ,, −CN, and −CHO substituents. Recently, we have reported direct coupling of ketones and amides for β-amino ketone synthesis under cobalt(III) catalysis and DMSO involvement; dibenzoylmethane couples with DMSO, with the participation of K 2 S 2 O 8 , to yield β-methylsulfide intermediate .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cyclopentenes and Cyclohexenes Via Cobalt(II)-Catalyzed Oxidative Cyclization

Shi

Chen

et al. 2021

J. Org. Chem.

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A unique method for the synthesis of cyclopentenes and cyclohexenes has been achieved by the coupling of diketones and alkenes under cobalt(II) catalysis and dimethyl sulfoxide involvement. Under optimal conditions, the formation of five- and six-membered rings can be readily controlled by the α-position substitution of styrenes. This process is proposed to proceed through a reaction sequence of oxidative coupling (mediated by K2S2O8), regioselective alkene insertion (promoted by cobalt), and intramolecular attack of the resulting allylcobalt species on the carbonyl group or methyl group in the reactive methylene process.

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One-Pot Formylation and Dimerization of p-Alkyl Phenols Using DCMT-Activated DMSO

Cited by 15 publications

References 14 publications

Dimethyl Sulfoxide Participant Iron-Mediated Cascade Oxidation/α-Formylation Reaction of Substituted 2,3-Dihydropyrroles under Air and Protonic Acid Free Condition

Dimethyl Sulfoxide Participant Iron-Mediated Cascade Oxidation/α-Formylation Reaction of Substituted 2,3-Dihydropyrroles under Air and Protonic Acid Free Condition

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Synthesis of Cyclopentenes and Cyclohexenes Via Cobalt(II)-Catalyzed Oxidative Cyclization

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