New examples of template catalysis based processes: glycerol-like units as efficient promoters for dehydrative nucleophilic substitutions of ferrocenylmethanol

Shisodia, Suresh U.; Auricchio, S.; Citterio, Attilio; Grassi, Marco Tadeu; Sebastiano, Roberto

doi:10.1016/j.tetlet.2013.12.034

Cited by 9 publications

(6 citation statements)

References 38 publications

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“…Serinol is an interesting polyfunctional molecule endowed with hydrogen donor groups and with the structural characteristics suitable, in principle, to promote dehydrative reactions based on template catalysis processes. 41,42 Considering the role of this possible component in the mechanism, we verified the reactivity of a couple of low polar, hydrophobic, monofunctional reactants like the n-octylamine and benzophenone. The reaction between these two molecules at 140 °C was fast and clean to give the corresponding imine (see Experimental Section).…”

Section: ■ Results and Discussionmentioning

confidence: 78%

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Environmentally Friendly and Regioselective One-Pot Synthesis of Imines and Oxazolidines Serinol Derivatives and Their Use for Rubber Cross-Linking

Barbera

Leonardi

Valerio

et al. 2020

ACS Sustainable Chem. Eng.

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High-yield regioselective synthesis of imines and oxazolidines derivatives of 2-amino-1,3-propandiol (serinol) was achieved by performing the reaction with aldehydes and ketones, in the absence of solvents and catalysts. Only imines were obtained when the carbonyl compound was aromatic and/or sterically hindered and when conjugated double bonds were formed. 1,3-Oxazolidines were specifically obtained with either aldehydes or ketones with limited steric hindrance. The "green" reaction conditions here adopted for the synthesis of these classes of derivatives are not due to the structural and functional peculiarity of the serinol as a reactant and can also be extended to lipophilic amines with the same good results in terms of yield and selectivity. A revision of the mechanism typically accepted in the presence of solvent and catalysis is proposed, and the quantum mechanics calculations applied to some derivatives are in good agreement with the proposed rationalizations of the selectivity observed. Serinol itself and the imine and oxazolidine derivatives were used, in place of guanidine, as accelerators in compounds based on diene rubbers and silica, suitable for application in tire treads with low environmental impact. Efficient sulfur-based cross-linking and composites with a low dissipation of energy were obtained. The oxazolidine and imine appear to act as protective groups of the serinol primary amine. This work paves the way for the selective synthesis of biosourced families of chemicals, which could be used for large-scale applications, such as the one in rubber compounds, replacing toxic oil-based chemicals.

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Section: ■ Results and Discussionmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Environmentally Friendly and Regioselective One-Pot Synthesis of Imines and Oxazolidines Serinol Derivatives and Their Use for Rubber Cross-Linking

Barbera

Leonardi

Valerio

et al. 2020

ACS Sustainable Chem. Eng.

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“…The compounds showed relatively low fungicidal activity. Instead, ferrocenyl ethers [22], much easier to prepare ( Figure 8) than previous diferrocenyl derivatives, showed moderate activity against two plant fungi, Botrytis cinerea and Penicillium species (Table 2).…”

Section: Ferrocene-containing Agrochemicalsmentioning

confidence: 99%

“…It has been produced since 1978, first as a racemic mixture, then (from 1997) as enantiomerically enriched [22] form, that allowed a 40% reduction of the environmental load. One of the most important strategies of asymmetric synthesis is the use of chiral catalysts.…”

Section: Ferrocenes As Catalysts In the Synthesis Of Agrochemicalsmentioning

confidence: 99%

Ferrocene in agriculture: from agrochemicals and soil remediation to selective chemosensors

Floris

2015

Chem. Biol. Technol. Agric.

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“…19 In this regard, hydroxymethylferrocene is a more versatile reagent, however for its activation, stoichiometric amounts of Brønsted acids (HSO 3 F, HBr, HBF 4 , HClO 4 , CH 3 CO 2 H, etc.) 19,20 are usually required (with a few exceptions 21 ), that impose some restrictions on the substrate scope. In recent years, much attention has been paid to nucleophilic substitution of the OH group in hydroxymethyl ferrocene using various metal-based catalysts.…”

Section: Introductionmentioning

confidence: 99%

Unexpected acid-catalyzed ferrocenylmethylation of diverse nucleophiles with vinyloxymethylferrocene

et al. 2016

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New examples of template catalysis based processes: glycerol-like units as efficient promoters for dehydrative nucleophilic substitutions of ferrocenylmethanol

Cited by 9 publications

References 38 publications

Environmentally Friendly and Regioselective One-Pot Synthesis of Imines and Oxazolidines Serinol Derivatives and Their Use for Rubber Cross-Linking

Environmentally Friendly and Regioselective One-Pot Synthesis of Imines and Oxazolidines Serinol Derivatives and Their Use for Rubber Cross-Linking

Ferrocene in agriculture: from agrochemicals and soil remediation to selective chemosensors

Unexpected acid-catalyzed ferrocenylmethylation of diverse nucleophiles with vinyloxymethylferrocene

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