The McMurry Coupling and Related Reactions

Ephritikhine, Michel; Villiers, Claude

doi:10.1002/3527601880.ch6

Cited by 12 publications

(3 citation statements)

References 247 publications

(311 reference statements)

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“…Our first encounter with uranium carbenes occurred in 1997 during our studies on the mechanism of the McMurry reaction, which is the reductive coupling of carbonyl compounds into alkenes upon treatment with low-valent titanium reagents [17]. Uranium and titanium complexes exhibit strong similarities in structure and reactivity, and uranium metal powder is effective in the reductive coupling of aromatic ketones.…”

Section: Uranium Carbenoid Species In Mcmurry Type Reactionsmentioning

confidence: 99%

Uranium carbene compounds

Ephritikhine

2013

Comptes Rendus. Chimie

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This article gives an overview of the development of uranium carbene complexes. The first example of these compounds was reported in 1981 with the phosphoylide complex Cp 3 U5CHPMe 2 Ph but nearly three decades passed before the area witnessed spectacular advances. During this time, actinide methylidene compounds were detected in solid argon, carbenoid uranium species were evidenced in McMurry type reactions, and a series of uranium complexes with N-heterocyclic carbene ligands was isolated. The recent developments in uranium carbene chemistry have to be related to the use of bisphosphorus stabilized geminal carbon dianions as ligands. Homoleptic complexes and a series of mixed chloro-, tetrahydroborato-, amido-, cyclopentadienyl-and cyclooctatetraenyl-carbene complexes of thorium(IV) and uranium in the +4, +5 and +6 oxidation states have been isolated and characterized. DFT calculations led to a good description of the U5C double bond that demonstrates a double s and p donation toward the metal atom with the involvement of the 5f orbitals.

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Section: Uranium Carbenoid Species In Mcmurry Type Reactionsmentioning

confidence: 99%

Uranium carbene compounds

Ephritikhine

2013

Comptes Rendus. Chimie

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“…Olefin-metathesis and the Heck reaction can circumvent certain limitations but they rely on pre-existing olefins. Different from the Wittig olefination, reductive carbonyl olefination such as the McMurry coupling [7][8][9][10] represents another powerful approach. With respect to the McMurry-type coupling, no reactive and basic nucleophiles are engaged, which is practically advantageous (Fig.…”

Section: Introductionmentioning

confidence: 99%

Olefination of aldehydes with alpha-halo redox-active esters

Liu,

Liu

2024

Org. Chem. Front.

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“…22 Many reviews have been discussing the latest in McMurry reaction such as the 2013 review by Takeda in Organic Reactions and the book "Modern Carbonyl Olenation: Methods and Applications". 23,24 In this review, we are summarizing and analyze the information, for the latest ve years, related to the McMurry reaction in several reviews, which consists of the type of reaction, general procedure, reagents, functional group compatibility, additives, and its application in the synthesis of natural and non-natural products. In addition, we will also discuss the advantages and disadvantages of the McMurry reaction, also the treatments to minimize the drawbacks of the McMurry reaction.…”

Section: Introductionmentioning

confidence: 99%