Iron‐Catalyzed Intermolecular 1,2‐Difunctionalization of Styrenes and Conjugated Alkenes with Silanes and Nucleophiles

Yang, Yuan; Song, Ren‐Jie; Ouyang, Xuan‐Hui; Wang, Chengyong; Li, Jin‐Heng; Luo, Shenglian

doi:10.1002/anie.201702349

Cited by 144 publications

(42 citation statements)

References 91 publications

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“…Organosilicon compounds have significant chemical, physical and bioactive properties and an example of these compounds is 1-amino-2-silylalkanes, which have, in recent times, emerged as candidates for pharmaceutical development. Silicon-containing compounds are generally made through hydrosylilation or dehydrogenative silylation, but in 2017 the group of Luo reported the first iron-catalyzed synthesis of 1-amino-2-silylalkanes through the 1,2-difunctionalization of styrenes and conjugated alkenes (Scheme 5) [23]. Di-tert-butyl-peroxide (DTBP) was used as an oxidant in the reaction.…”

Section: Addition Reactionsmentioning

confidence: 99%

On the Use of Iron in Organic Chemistry

Guðmundsson

Bäckvall

2020

Molecules

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Transition metal catalysis in modern organic synthesis has largely focused on noble transition metals like palladium, platinum and ruthenium. The toxicity and low abundance of these metals, however, has led to a rising focus on the development of the more sustainable base metals like iron, copper and nickel for use in catalysis. Iron is a particularly good candidate for this purpose due to its abundance, wide redox potential range, and the ease with which its properties can be tuned through the exploitation of its multiple oxidation states, electron spin states and redox potential. This is a fact made clear by all life on Earth, where iron is used as a cornerstone in the chemistry of living processes. In this mini review, we report on the general advancements in the field of iron catalysis in organic chemistry covering addition reactions, C-H activation, cross-coupling reactions, cycloadditions, isomerization and redox reactions.

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Section: Addition Reactionsmentioning

confidence: 99%

On the Use of Iron in Organic Chemistry

Guðmundsson

Bäckvall

2020

Molecules

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“…Recently, we reported an iron‐catalyzed 1,2‐difunctionalization of styrenes and alkenes with silanes and other nucleophiles. Using FeCl 2 as the catalysts and di‐ tert ‐butyl peroxide as the oxidant, the 1,2‐difunctionalizations, including 1,2‐aminosilylation, 1,2‐arylsilylation, and 1,2‐alkylsilylation were performed (Scheme ) . A wide range of nucleophiles, such as amines, amides, indoles, pyrroles, and 1,3‐dicarbonyls, compatible with the conditions to afford the silicon‐containing alkanes.…”

Section: 2‐diheterofunctionalizationmentioning

confidence: 99%

Recent Advances in the Intermolecular Oxidative Difunctionalization of Alkenes

Lin

Song

et al. 2018

The Chemical Record

158

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Functionalization of alkenes has been well investigated by chemists, thus it has been extensively applied in organic synthesis and industries. In the past few decades, transition-metal, such as palladium, rhodium, gold, iridium, copper and iron, catalyzed functionalization reactions of alkenes have been significantly developed and played vital roles in synthesis. The difunctionalization of alkenes are appealing as an important alternative to the traditional approaches for the construction of useful carbon centers, particularly carbon quaternary centers, which commonly existed as structural motifs in numerous natural products, pharmaceuticals, and biologically active molecules. This account will summarize our recent advances in the intermolecular difunctionalization of alkenes, and also highlight the scope and limitations as well as the mechanisms of these difunctionalization reactions. In general, in this account the difunctionalization of alkenes starting from dicarbofunctionalization will be discussed. Then carboheterofunctionalization of alkenes will be intensively reviewed, and diheterofunctionalization will also be highlighted.

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“…Oxidative coupling processes, where iron salts and complexes serve as oxidants or their precursors, are becoming more and more popular. A number of oxidative coupling reactions, accompanied by formation of C‐C, C‐N, C‐P, C‐S, C‐O, C‐Si bonds, mediated by iron compounds, were discovered.…”

Section: Introductionmentioning

confidence: 99%

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β‐Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron‐Based Oxidants

et al. 2019

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Selectivity of sulfonylation of β‐keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α‐Sulfonyl β‐keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α‐sulfonyl esters – the products of successive sulfonylation‐deacylation. When β‐diketones are applied as starting materials, only α‐sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α‐sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation‐deacylation. Participation of the solvent in the reaction pathway determines the products structure.

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Iron‐Catalyzed Intermolecular 1,2‐Difunctionalization of Styrenes and Conjugated Alkenes with Silanes and Nucleophiles

Cited by 144 publications

References 91 publications

On the Use of Iron in Organic Chemistry

On the Use of Iron in Organic Chemistry

Recent Advances in the Intermolecular Oxidative Difunctionalization of Alkenes

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β‐Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron‐Based Oxidants

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