Wacker‐Tsuji‐Type Oxidation Reactions of Styrene Derivatives Catalyzed by Ferrate

Hashimoto, Toru; Maruyama, Tsubasa; Ishimaru, Toshiya; Matsugaki, Masaru; Shiota, Keisuke; Yamaguchi, Yoshitaka

doi:10.1002/slct.202101752

Cited by 7 publications

(4 citation statements)

References 31 publications

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“…Similarly, Yamaguchi and co‐workers developed an iron‐catalyzed Wacker‐type oxidation of styrenes to ketones by utilizing 5 mol % of a ferrate Fe III complex as precatalyst (Scheme 14). [31] The reaction conditions are similar to those reported independently by the groups of Han and Knölker. They consist of TMDS (TMDS=1,1,3,3‐tetramethyldisiloxane) as the reducing agent in ethanol at 80 °C in an O 2 atmosphere.…”

Section: Iron‐based Catalysts For Wacker‐type Reactionssupporting

confidence: 80%

“…Similarly, Yamaguchi and co-workers developed an ironcatalyzed Wacker-type oxidation of styrenes to ketones by utilizing 5 mol % of a ferrate Fe III complex as precatalyst (Scheme 14). [31] The reaction conditions are similar to those Scheme 10. Postulated reaction mechanism for the Wacker-type oxidation of terminal olefins to ketones catalyzed by a hexadecafluorinated iron(II) phthalocyanine (the phthalocyanine ligand around the iron center is not depicted for the sake of clarity).…”

Section: Iron-based Catalysts With Markovnikov Selectivitymentioning

confidence: 99%

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Sustainable Wacker‐Type Oxidations

et al. 2022

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The Wacker reaction is the oxidation of olefins to ketones and typically requires expensive and scarce palladium catalysts in the presence of an additional copper co-catalyst under harsh conditions (acidic media, high pressure of air/dioxygen, elevated temperatures). Such a transformation is relevant for industry, as shown by the synthesis of acetaldehyde from ethylene as well as for fine-chemicals, because of the versatility of a carbonyl group placed at specific positions. In this regard, many contributions have focused on controlling the chemo-and regioselectivity of the olefin oxidation by means of well-defined palladium catalysts under different sets of reaction conditions. However, the development of Wacker-type processes that avoid the use of palladium catalysts has just emerged in the last few years, thereby paving the way for the generation of more sustainable procedures, including milder reaction conditions and green chemistry technologies. In this Minireview, we discuss the development of new catalytic processes that utilize more benign catalysts and sustainable reaction conditions.

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Section: Iron‐based Catalysts For Wacker‐type Reactionssupporting

confidence: 80%

Section: Iron-based Catalysts With Markovnikov Selectivitymentioning

confidence: 99%

Sustainable Wacker‐Type Oxidations

et al. 2022

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“…A similar strategy was also developed by Yamaguchi and co-workers for an air-and moisture-stable bis(triphenylphosphoranylidene)ammonium ferrate (PPN)[FeCl 4 ]-catalyzed Wacker-type oxidation of styrenes to ketones by utilizing molecular oxygen as the sole oxidant. 26 Scheme 6 Iron-catalyzed Wacker-oxidation under air at room temperature Y. Gao et al…”

Section: Methodsmentioning

confidence: 99%

New Paradigms in Catalysis Inspired by Cytochromes P450

Gao

Cheng

Shi

et al. 2023

Synlett

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Cytochromes P450 (P450s or CYPs) are versatile biocatalysts capable of realizing a broad range of synthetically challenging reactions. The development of synthetic catalysts/catalytic systems that model the enzyme function is a goal that has long been pursued. In this account, we mainly summarize our latest advances in the field of P450s-inspired catalysis, including reductive activation strategy for highly efficient oxidations and an unusual L-cystine-derived ligand as the model of the P450s for highly efficient iron-catalyzed undirected arene C-H hydroxylation. These new paradigms exhibit some catalytic properties of P450s, such as effective late-stage functionalization of complex targets, good reactive functional group tolerance, and high catalytic efficiency and selectivity. 1. Introduction 2. Reductive activation strategy for oxygenation 3. Fe/Cysteine-based ligand as a biomimetic model of P450 for arene C-H hydroxylation 4. Conclusion

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“…Therefore, many catalysts, especially Brønsted acids or Lewis acids, have been developed for the synthesis of β-alkoxy alcohols. [5][6][7][8][9] As a part of our ongoing project on transformations of organic molecules using organosilicon compounds, [10] we found that commercially available Ph 3 SiH works as a Lewis-acidic catalyst for the ring-opening reactions of di-and tri-substituted epoxides with alcohols. Herein, we report a simple method for the synthesis of β-alkoxy alcohols via the ring-opening reaction of di-and tri-substituted epoxides by alcohols using inexpensive and benign Ph 3 SiH as a catalyst under nearly neutral reaction conditions (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%