Fe‐Catalyzed Thioesterification of Carboxylic Esters

Magens, Silja; Plietker, Bernd

doi:10.1002/chem.201101073

Cited by 54 publications

(15 citation statements)

References 59 publications

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“…Low‐valent structurally defined ferrates such as Bu 4 N[Fe(CO) 3 (NO)] (TBAFe) have proved to be versatile catalysts for, for example, allylic substitutions,9a,9b hydrosilylations,9c or transesterifications 9d,9e. Recently we published a paper on the two‐ or three‐component TBAFe‐catalysed alkoxy‐allylation of electron‐deficient olefins10a (Scheme , top).…”

Section: Introductionmentioning

confidence: 99%

The Fe‐Catalysed Phosphono‐Allylation of Activated Olefins

Rommel¹,

Dieskau²,

Plietker³

2013

Eur J Org Chem

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Phosphonates are useful building blocks for organic synthesis, and are also bioactive compounds. Traditionally, they are prepared by nucleophilic substitution under thermal conditions. The preparation of more densely functionalized phosphonates is still a synthetic challenge. In this paper, we present a convenient one‐pot three‐component phosphono‐allylation of activated olefins to give phosphonates bearing a variety of functional groups.

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Section: Introductionmentioning

confidence: 99%

The Fe‐Catalysed Phosphono‐Allylation of Activated Olefins

Rommel¹,

Dieskau²,

Plietker³

2013

Eur J Org Chem

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“…Organosilicon components were versatile for the coupling as well ( 3j – n ). Estratrien, a kind of female hormone drug, was readily applied to late-stage diversification affording corresponding sulfur-modified estratrien 3o . Thioesters are important building blocks widespread in biochemistry .…”

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confidence: 99%

Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis

2016

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A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was obtained under ligand-free conditions in which disulfide generated from homocoupling could be prevented. Meanwhile, application of bidentate phosphine ligands under carbon monoxide atmosphere (CO balloon) afforded the thioester with little decomposition, which was revealed through interval NMR tracking.

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“…Benzyl 3-Phenylpropanethioate (3aj). 32 Reaction with Water (2k). The reaction was performed according to the general procedure in water (2k) (0.30 mL) and tBuOH (0.10 mL).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

C–C Bond Cleavage of Unactivated 2-Acylimidazoles

et al. 2020

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2-Acylimidazoles are widely used as post-transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C−C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C−C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

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Fe‐Catalyzed Thioesterification of Carboxylic Esters

Cited by 54 publications

References 59 publications

The Fe‐Catalysed Phosphono‐Allylation of Activated Olefins

The Fe‐Catalysed Phosphono‐Allylation of Activated Olefins

Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis

C–C Bond Cleavage of Unactivated 2-Acylimidazoles

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