Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes

Evano, Gwilherm; Gaumont, Annie‐Claude; Alayrac, C.; Wrona, Iwona E.; Giguere, Joshua R.; Delacroix, Olivier; Bayle, Alexandre; Jouvin, Kévin; Theunissen, Cédric; Gatignol, Jérémie; Silvanus, Andrew C.

doi:10.1016/j.tet.2013.11.073

Cited by 72 publications

(41 citation statements)

References 545 publications

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“…Although such transformations have been continuously developed by means of transition metal catalysis, 126 silver-catalysed protocols remain rather rare. Although such transformations have been continuously developed by means of transition metal catalysis, 126 silver-catalysed protocols remain rather rare.…”

Section: Intermolecular Hydroaminationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

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Section: Intermolecular Hydroaminationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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“…Enamides constitute a readily accessible 1 and versatile class of nitrogen-containing building blocks which can be used in a wide array of transformations.…”

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confidence: 99%

PIFA-mediated ethoxyiodination of enamides with potassium iodide

et al. 2016

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The regioselective ethoxyiodination of enamides was developed using PIFA in combination with potassium iodide in ethanol. The reaction proceeds regioselectively with excellent yields and diastereoselectivities, providing valuable synthons for further functionalisations. Control experiments were conducted, indicating that the transformation occurs through an ionic manifold involving an in situ generated hypoiodite species.

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“…However, it should be noted that in most studies, organic halides are used as aromatic substrates, while the examples of the C7H bond substitution with the hydrogen atom being the leaving group are far fewer. In reviews devoted to the metal-catalyzed C7P bond formation published in recent years, 16,17,58 virtually no consideration is given to aromatic C7H bond phosphorylation. Catalytic methods, the role of which is of particular importance for green chemistry, came into active development rather recently.…”

Section: Methodsmentioning

confidence: 99%