Recent advances in the synthesis of ferrocene derivatives <i>via</i> 3d transition metal-catalyzed C–H functionalization

Zhang, Zhuo‐Zhuo; Huang, Dan-Ying; Shi, Bing‐Feng

doi:10.1039/d2ob00558a

Cited by 21 publications

(7 citation statements)

References 92 publications

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“…4. Several publications reported efficient C-H functionalization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ees [145].…”

Section: Preparation Of Planar Chiral Ferrocenes: Asymmetric Synthesi...mentioning

confidence: 99%

“…alization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ees [145].…”

Section: Several Publications Reported Efficient C-h Function-mentioning

confidence: 99%

“… The direct Pd‐catalysed asymmetric C–H acylation of 1‐dimethylaminomethylferrocene generated compounds 36 with high ee s for insertion of arylketones (R = Ar), but a lower ee was obtained in the case of methylketone (R = Me) [ 40 ]. Several publications reported efficient C–H functionalization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ee s [ 145 ]. The enantioselective alkylation of amidoferrocene with diethylmalonate generated compounds 37 with ee s between 64% and 88% [ 146 ].…”

Section: Planar Chiral Ferrocenesmentioning

confidence: 99%

“…Several publications reported efficient C–H functionalization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ee s [ 145 ]. The enantioselective alkylation of amidoferrocene with diethylmalonate generated compounds 37 with ee s between 64% and 88% [ 146 ].…”

Section: Planar Chiral Ferrocenesmentioning

confidence: 99%

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Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

Peluso

Mamane

2022

Electrophoresis

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In the last decade, planar chiral ferrocenes have attracted a growing interest in several fields, particularly in asymmetric catalysis, medicinal chemistry, chiroptical spectroscopy and electrochemistry. In this frame, the access to pure or enriched enantiomers of planar chiral ferrocenes has become essential, relying on the availability of efficient asymmetric synthesis procedures and enantioseparation methods. Despite this, in enantioseparation science, these metallocenes were not comprehensively explored, and very few systematic analytical studies were reported in this field so far. On the other hand, enantioselective highperformance liquid chromatography has been frequently used by organic and organometallic chemists in order to measure the enantiomeric purity of planar chiral ferrocenes prepared by asymmetric synthesis. On these bases, this review aims to provide the reader with a comprehensive overview on the enantioseparation of planar chiral ferrocenes by discussing liquid-phase enantioseparation methods developed over time, integrating this main topic with the most relevant aspects of ferrocene chemistry. Thus, the main structural features of ferrocenes and the methods to model this class of metallocenes will be briefly summarized. In addition, planar chiral ferrocenes of applicative interest as well as the limits of asymmetric synthesis for the preparation of some classes of planar chiral ferrocenes will also be discussed with the aim to orient analytical scientists towards 'hot topics' and issues which are still open for accessing enantiomers of ferrocenes featured by planar chirality.

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“…4. Several publications reported efficient C-H functionalization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ees [145].…”

Section: Preparation Of Planar Chiral Ferrocenes: Asymmetric Synthesi...mentioning

confidence: 99%

“…alization methods for the synthesis of planar chiral ferrocenes that generally resulted in moderate ees [145].…”

Section: Several Publications Reported Efficient C-h Function-mentioning

confidence: 99%

Section: Planar Chiral Ferrocenesmentioning

confidence: 99%

Section: Planar Chiral Ferrocenesmentioning

confidence: 99%

See 2 more Smart Citations

Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

Peluso

Mamane

2022

Electrophoresis

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“…Moreover, many elegant strategies employing transition-metal-catalyzed C–H glycosylation were subsequently developed by the groups of Chen and He, , Liang and Liu, Liu, Akermann, and others . But to the best of our knowledge, ferrocene derivatives have not been employed for this C–H glycosylation so far . In continuation of our constant effort toward transition-metal-catalyzed C–H functionalization of ferrocene derivatives, we herein disclosed a Pd-catalyzed stereoselective dual C–H bond glycosylation of ferrocenyl amides with convenient glycosyl chlorides (Scheme c).…”

mentioning

confidence: 99%

Highly Stereoselective Synthesis of Bis-C-ferrocenyl Glycosides via Palladium-Catalyzed Directed C–H Glycosylation

Zhang

et al. 2023

Org. Lett.

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Conjugation of carbohydrates to ferrocene scaffolds is of great value in drug design, given the nontoxic and lipophilic nature of ferrocene. However, the efficient and stereoselective synthesis of C-ferrocenyl glycosides remains a challenge. Herein, we developed a Pd-catalyzed stereoselective C–H glycosylation to provide rapid access to sole bis-C-ferrocenyl glycosides in good to high yields (up to 98% yield) with exclusive stereoselectivity. A diverse range of glycosyl chlorides were well tolerated, including d-mannose, d-glucose, l-xylose, l-rhamnose, d-mannofuranose, and d-ribofuranose. Additionally, a mononuclear PdII intermediate was characterized by X-ray single-crystal diffraction, and might participate in the C–H palladation step.

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Synthesis of Complex Dihydroisoquinolin Derivatives via Cobalt‐Electrocatalyzed C−H Activation

Dong

Huang

2023

Adv Synth Catal

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We developed a cost‐effective cobalt‐catalyzed electrochemical annulation to generate diversified novel complex dihydroisoquinolin derivatives from amides and alkenes in a simple and maneuverable undivided cell. The reaction proceeded C−H/N−H activation, and the catalyst was regenerated by anodic oxidation. Notably, the strategy of electrocatalysis avoided the consumption of stoichiometric chemical oxidants.

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Recent advances in the synthesis of ferrocene derivatives via 3d transition metal-catalyzed C–H functionalization

Abstract: A review of recent advances in the construction of racemic and chiral ferrocene derivatives via 3d transition metal-catalyzed C–H activation.

Cited by 21 publications

References 92 publications

Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

Highly Stereoselective Synthesis of Bis-C-ferrocenyl Glycosides via Palladium-Catalyzed Directed C–H Glycosylation

Synthesis of Complex Dihydroisoquinolin Derivatives via Cobalt‐Electrocatalyzed C−H Activation

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