Iron-Catalyzed Carbonyl–Alkyne and Carbonyl–Olefin Metathesis Reactions

Grau, Benedikt W.; Tsogoeva, Svetlana B.

doi:10.3390/catal10091092

Cited by 6 publications

(1 citation statement)

References 46 publications

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“… [5] In 2005, Chauvin, Grubbs and Schrock were awarded with the Nobel prize in chemistry for their pioneering work on olefin metathesis. [6] In addition to the olefin−olefin metathesis reaction, recently reported carbonyl−alkyne [7] and carbonyl−olefin[ 7b , 8 ] metathesis reactions further expand the space of synthetically available structures. However, the latter do not follow the Chauvin mechanism and the use of different types of catalysts is required, for example, Lewis acids.…”

Section: Introductionmentioning

confidence: 99%

Iron‐Catalyzed Olefin Metathesis: Recent Theoretical and Experimental Advances

Grau

Neuhauser

Aghazada

et al. 2022

Chemistry A European J

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The "metathesis reaction" is a straightforward and often metal-catalyzed chemical reaction that transforms two hydrocarbon molecules to two new hydrocarbons by exchange of molecular fragments. Alkane, alkene and alkyne metathesis have become an important tool in synthetic chemistry and have provided access to complex organic structures. Since the discovery of industrial olefin metathesis in the 1960s, many modifications have been reported; thus, increasing scope and improving reaction selectivity. Olefin metathesis catalysts based on high-valent group six elements or Ru(IV) have been developed and improved through ligand modifications. In addition, significant effort was invested to realize olefin metathesis with a non-toxic, bio-compatible and one of the most abundant elements in the earth's crust; namely, iron. First evidences suggest that low-valent Fe(II) complexes are active in olefin metathesis. Although the latter has not been unambiguously established, this review summarizes the key advances in the field and aims to guide through the challenges.

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Section: Introductionmentioning

confidence: 99%

Iron‐Catalyzed Olefin Metathesis: Recent Theoretical and Experimental Advances

Grau

Neuhauser

Aghazada

et al. 2022

Chemistry A European J

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Recent Advances on Synthesis of 2H‐Chromenes, and Chromenes Fused Hetrocyclic Compounds

Kumar Maurya,

Dey,

Kumara

et al. 2024

Asian J Org Chem

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Chromenes and 2H‐Chromenes are vital components of natural products, pharmaceuticals, and agrochemicals that have captured the attention of researchers worldwide. These heterocyclic compounds represent an essential class of structural scaffolds, and the quest for their synthesis in a mild and straightforward way has gained significant momentum. Chromenes are oxygen‐containing heterocycles that have been widely studied due to their potential medicinal properties. In the last two decades, researchers have made remarkable progress towards the synthesis of chromene based heterocyclic compounds using O‐propargylated benzaldehydes as a substrate. These substrates are highly versatile and contain functional groups that make them ideal for a wide range of reactions. This review article provides an in‐depth analysis of the latest advances in alkynes' functionalization, emphasizing the substrate scope, limitations, regioselectivity control, and applications of these reactions. The review also covers a range of critical methods and strategies, including multicomponent reactions, used for the general synthesis of numerous types of chromene derivatives.

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Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

Arndt,

Breugst

2024

Chemistry A European J

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The reaction between aldehydes or ketones and alkynes –the carbonyl‐alkyne metathesis– constitutes a very useful strategy for the synthesis of a,b‐unsaturated carbonyls. We now demonstrate that iodine is a highly efficient catalyst for both the intra‐ and intermolecular metathesis reaction in very small concentrations (0.1–1 mol%). Our protocol outperforms other catalytic systems, is operationally very simple, cheap, metal‐free, and tolerates a large variety of functional groups (e.g., –CN, –CO2Me, –Br, –OH) at very low catalyst loadings. We can furthermore show that iodine‐catalyzed carbonyl‐alkyne metatheses can be combined with other iodine‐catalyzed reactions in one‐pot procedures to afford larger and more complex molecular structures. Finally, our mechanistic studies indicate that the iodonium ion is the active catalyst under the reaction conditions.

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Iron-Catalyzed Carbonyl–Alkyne and Carbonyl–Olefin Metathesis Reactions

Cited by 6 publications

References 46 publications

Iron‐Catalyzed Olefin Metathesis: Recent Theoretical and Experimental Advances

Iron‐Catalyzed Olefin Metathesis: Recent Theoretical and Experimental Advances

Recent Advances on Synthesis of 2H‐Chromenes, and Chromenes Fused Hetrocyclic Compounds

Iodine‐Catalyzed Carbonyl‐Alkyne Metathesis Reactions

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