Fe-Catalyzed Dicarbofunctionalization of Vinylarenes with Alkylsilyl Peroxides and β-Keto Carbonyl Substrates

Wang, Xu; Kato, Terumasa; Liu, Yan; Matsumoto, Akira; Maruoka, Keiji

doi:10.1021/acs.orglett.2c00656

Cited by 11 publications

(3 citation statements)

References 44 publications

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“…In 2022, Maruoka et al realized a novel and synthetically attractive one-pot three-component coupling reaction for the dicarbofunctionalization of different vinyl-arenes 15 with a wide array of β-keto-carbonyl substrates 16 and various alkyl silyl peroxide 14 via a radical pathway in the presence of Fe(OTf) 2 catalyst under mild conditions with good diastereoselectivity (Scheme 3). [44] Initially, they explored optimization conditions by utilizing 4-methoxystyrene, alkylsilyl peroxide, and methylacetoacetate as model substrates. Optimization study revealed that the use of 10 mol % Fe(OTf) 2 as a catalyst, and 0.2 M dioxane as solvent at 40 °C for 12 h furnished the desired product in good to excellent yield.…”

Section: Iron-catalyzed Dicarbofunctionalization Reactionsmentioning

confidence: 99%

The Recent Advances in Iron‐Catalyzed C(sp³)−H Functionalization

Bhavyesh,

Soliya,

Konakanchi

et al. 2024

Chemistry An Asian Journal

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The use of iron as a core metal in catalysis has become a research topic of interest over the last few decades. The reasons are clear. Iron is the most abundant transition metal on Earth’s crust and it is widely distributed across the world. It has been extracted and processed since the dawn of civilization. All these features render iron a noncontaminant, biocompatible, nontoxic, and inexpensive metal and therefore it constitutes the perfect candidate to replace noble metals (rhodium, palladium, platinum, iridium, etc.). Moreover, direct C–H functionalization is one of the most efficient strategies by which to introduce new functional groups into small organic molecules. The majority of organic compounds contain C(sp3)–H bonds. Given the enormous importance of organic molecules in so many aspects of existence, the utilization and bioactivity of C(sp3)–H bonds are of the utmost importance. This review sheds light on the substrate scope, selectivity, benefits, and limitations of iron catalysts for direct C(sp3)–H bond activations. An overview of the use of iron catalysis in C(sp3)–H activation protocols is summarized herein up to 2022.

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Section: Iron-catalyzed Dicarbofunctionalization Reactionsmentioning

confidence: 99%

The Recent Advances in Iron‐Catalyzed C(sp³)−H Functionalization

Bhavyesh,

Soliya,

Konakanchi

et al. 2024

Chemistry An Asian Journal

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“…Vinylarenes with various substituents, along with numerous alkylsilyl peroxides 76 and β-keto carbonyl substrates 57, can be employed in this process. Using the same reaction conditions, a novel benzopyran derivative 78 was created from 2-hydroxystyrene, which is an important molecule with various biological characteristics (Xu et al, 2022).…”

Section: Ironmentioning

confidence: 99%

Recent progress in metal assisted multicomponent reactions in organic synthesis

Sakthivel,

Gana,

Shoji

et al. 2023

Front. Chem.

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To prepare complicated organic molecules, straightforward, sustainable, and clean methodologies are urgently required. Thus, researchers are attempting to develop imaginative approaches. Metal-catalyzed multicomponent reactions (MCRs) offer optimal molecular diversity, high atomic efficiency, and energy savings in a single reaction step. These versatile protocols are often used to synthesize numerous natural compounds, heterocyclic molecules, and medications. Thus far, the majority of metal-catalyzed MCRs under investigation are based on metal catalysts such as copper and palladium; however, current research is focused on developing novel, environmentally friendly catalytic systems. In this regard, this study demonstrates the effectiveness of metal catalysts in MCRs. The aim of this study is to provide an overview of metal catalysts for safe application in MCRs.

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“…We have recently developed Cu-, Fe-, and Ni-catalyzed radical approaches − for the generation of alkyl radicals from alkylsilyl peroxides that proceed under mild reductive conditions (via a reductive β-scission strategy) . During the course of our investigations of the transformations with alkylsilyl peroxides, we initially reported the Cu-catalyzed mono- N -alkylation of amides, in which no N , N -dialkylation products were detected under ordinary reaction conditions (Scheme b) .…”

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confidence: 99%