ChemInform Abstract: Four‐ and Sixfold Tandem‐Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches.

Tietze, Lutz F.; Waldecker, Bernd; Ganapathy, Dhandapani; Eichhorst, Christoph; Lenzer, Thomas; Oum, Kawon; Reichmann, Sven

doi:10.1002/chin.201603136

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“…4−6 Looking back, the precise synthesis of complex compounds has been the ultimate goal in the field of synthetic chemistry. 7−9 To achieve the above goal, chemists have discovered and developed various synthetic strategies, 10,11 among which metal-ion coordination-catalyzed localization activation is one of the most widely used strategies. 12−14 Given that the traditional metal-ion coordination catalytic activation undergoes a coordination−activation (direction)−leaving catalytic process (Scheme 1a), it is difficult to achieve multiple localization activation (tandem activation) of the starting reaction materials.…”

Section: ■ Introductionmentioning

confidence: 99%

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“One-Pot” In Situ Tandem Reaction─Dy(III) Coordination-Catalyzed Multicomponent Condensation of Salicylaldehyde Derivatives to Obtain Ketals

Wang

et al. 2023

Inorg. Chem.

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It is difficult to subject simple reaction starting materials to a “one-pot” in situ tandem reaction without post-treatment under mild reaction conditions to obtain multimers with complex structural linkages. In organic synthesis, acetal reactions are often used to protect derivatives containing carbonyl functional groups. Therefore, acetal products tend to have very low stability, and performing multi-step condensation to obtain complex multimeric products is difficult. Herein, we achieved the first efficient multiple condensation of o-vanillin derivatives using Dy(OAc)3·6H2O undergoing a “one-pot” in situ tandem reaction under mild solvothermal conditions to obtain a series of dimers (I and II, clusters 1 and 2) and trimers (I and II, clusters 3 and 4). When methanol or ethanol is used as the solvent, the alcoholic solvent participates in acetal and dehydration reactions to obtain dimers (I and II). Surprisingly, when using acetonitrile as the reaction solvent, the o-vanillin derivatives undergo acetal and dehydration reactions to obtain trimers (I and II). In addition, clusters 1–4 all showed distinct single-molecule magnetic behaviors under zero-field conditions. To the best of our knowledge, this is the first time that multiple acetal reactions catalyzed by coordination-directed catalysis under “one-pot” conditions have been realized, opening a new horizon for the development of fast, facile, green, and efficient synthetic methods for complex compounds.

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Section: ■ Introductionmentioning

confidence: 99%

“…When the reaction reached 12 h, fragment (7) S11). After 48 h of reaction, fragment (9) was largely consumed to produce fragment (10) S11). Therefore, the possible formation mechanism of the trimer is speculated S3).…”

Section: ■ Introductionmentioning

confidence: 99%

“One-Pot” In Situ Tandem Reaction─Dy(III) Coordination-Catalyzed Multicomponent Condensation of Salicylaldehyde Derivatives to Obtain Ketals

Wang

et al. 2023

Inorg. Chem.

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ChemInform Abstract: Four‐ and Sixfold Tandem‐Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches.

Abstract: Tetrasubstituted alkenes (II) and (IV) with intrinsic helical chirality are prepared via a fourfold tandem‐domino reaction consisting of two carbopalladation and two C—H activation steps.

Cited by 1 publication

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“One-Pot” In Situ Tandem Reaction─Dy(III) Coordination-Catalyzed Multicomponent Condensation of Salicylaldehyde Derivatives to Obtain Ketals

“One-Pot” In Situ Tandem Reaction─Dy(III) Coordination-Catalyzed Multicomponent Condensation of Salicylaldehyde Derivatives to Obtain Ketals

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