Palladium-catalyzed synthesis of mixed anhydrides<i>via</i>carbonylative telomerization

Hares, Kevin; Vogelsang, Dennis; Wernsdörfer, Charlotte S.; Panke, Dennis; Vogt, Dieter; Seidensticker, Thomas

doi:10.1039/d2cy00486k

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…However, they have been isolated with moderate yields. In the same year, Seidensticker et al [20] reported a new palladium acetate Pd (OAc) 2 ‐catalyzed synthesis of carboxylic acid anhydrides via the telomerization of 1,3‐butadiene and carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Response surface methodology based on the Box‐Behnken design for optimizing the synthesis of symmetrical anhydrides from acid chlorides using cerium (III) as a homogeneous catalyst

Larba,

Boukachabia,

Zeror

et al. 2023

ChemistrySelect

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Here we report the synthesis of symmetrical carboxylic acid anhydrides from acid chlorides using cerium (III) as a homogeneous catalyst. The optimal experimental conditions (temperature at 40 °C, catalyst loading at 30 mg, 1.5 equivalents of base, and solvent volume at 1 mL) for the preparation of benzoic anhydride 2 a were obtained using the Box‐Behnken design in combination with the response‐surface methodology. The analysis of variance showed that the presented quadratic model successfully performed the experimental data with coefficients of determination of R2=0.99. The predicted yield of synthesized anhydride 2 a obtained from the RSM under optimal conditions was 98.63 %. A confirmation test of the optimal conditions proved the viability of the model and gave a yield of 97.27 %. Under the optimal conditions, the resulting synthesized anhydrides 2 a–g were obtained with good isolated chemical yields of 60 %

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Section: Introductionmentioning

confidence: 99%

Response surface methodology based on the Box‐Behnken design for optimizing the synthesis of symmetrical anhydrides from acid chlorides using cerium (III) as a homogeneous catalyst

Larba,

Boukachabia,

Zeror

et al. 2023

ChemistrySelect

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“…Recently, Seidensticker and co‐workers reported on the carbonylative telomerization of 1,3‐butadiene with carboxylic acids. This produced mixed 3,8‐nonadienoic anhydrides which were directly used as acetylation agents for the synthesis of amides [8] …”

Section: Introductionmentioning

confidence: 99%

“…This produced mixed 3,8nonadienoic anhydrides which were directly used as acetylation agents for the synthesis of amides. [8] Acetic anhydride can be produced via the ketene process, [1] oxidation of acetaldehyde [1] or via the carbonylation of methyl acetate. [1,9] The ketene process can also be used for the synthesis of long chain anhydrides.…”

Section: Introductionmentioning

confidence: 99%

Reppe‐Carbonylation of Alkenes with Carboxylic Acids: A Catalytic and Mechanistic Study

et al. 2022

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In this work, a green‐catalytic procedure is used to demonstrate the synthesis of long‐chain anhydrides. This is accomplished by the carbonylation of alkenes with carboxylic acids. Anhydrides are important intermediates, finding specific applications as acetylation agents. The process is catalyzed by a Pd phosphine catalyst system in the presence of an acid promotor. Through optimization experiments, the importance of the phosphine ligand and acid promotor is demonstrated, without which the catalyst shows no activity. Although the yield was limited because of catalyst deactivation (42 %), to the best of our knowledge, the synthesis of long‐chain anhydrides through this route have not been reported previously. It therefore represents a significant result. Isolation of the anhydrides were also successfully demonstrated, however, as a result of the sensitivity of the anhydrides to water, the isolated yields were much lower than the HPLC yield. Furthermore, a mechanistic study by means of HP‐NMR (High Pressure Nuclear Magnetic Resonance) spectroscopy provided significant insights into the mechanism of the reaction.

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Boosting the feasibility of heterogeneous telomerization of 1,3-butadiene with methanol by low-surface-area N-heterocyclic carbene-functionalized hypercrosslinked polymers

Zhang,

Yu,

Zhao

et al. 2024

Chemical Engineering Journal

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Palladium-catalyzed synthesis of mixed anhydridesviacarbonylative telomerization

Abstract: For the first time, mixed carboxylic anhydrides were accessed directly via homogeneous palladium catalysis from 1,3-butadiene and carboxylic acids. Under carbonylative telomerization conditions, the respective mixed 3,8-nonadienoic anhydrides are formed...

Cited by 5 publications

References 28 publications

Response surface methodology based on the Box‐Behnken design for optimizing the synthesis of symmetrical anhydrides from acid chlorides using cerium (III) as a homogeneous catalyst

Response surface methodology based on the Box‐Behnken design for optimizing the synthesis of symmetrical anhydrides from acid chlorides using cerium (III) as a homogeneous catalyst

Reppe‐Carbonylation of Alkenes with Carboxylic Acids: A Catalytic and Mechanistic Study

Boosting the feasibility of heterogeneous telomerization of 1,3-butadiene with methanol by low-surface-area N-heterocyclic carbene-functionalized hypercrosslinked polymers

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