An Unusual Ruthenium-Catalyzed Dimerization of Propargyl Alcohols

Trost, Barry M.; Rudd, Michael T.

doi:10.1021/ja0111636

Cited by 42 publications

(24 citation statements)

References 6 publications

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“…In fact, this dehydro dimer was formed as the single reaction product when the reaction was carried out in the absence of 2-bromothiophene. The dimerization of the propargyl alcohol is reported in the literature to occur with ruthenium catalysts, [10] but so far no reaction involving the use of a palladium catalyst has been reported. Substituents [b] Method [c] [a] Aromatic ring bound to C-3.…”

Section: Synthesis Of Propargyl Alcoholsmentioning

confidence: 98%

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

et al. 2011

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International audienceHerein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes

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Section: Synthesis Of Propargyl Alcoholsmentioning

confidence: 98%

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

et al. 2011

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“…(77)]. [234] The conditions of the reaction have been optimized to yield exclusively the a,b-Z olefin isomer, as well as a single g,d geometrical isomer if there is branching in the alkyl substituent.…”

Section: Ruthenium-catalyzed Alkyne-alkyne and Diyne-coupling Reactionsmentioning

confidence: 99%

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

2005

Self Cite

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The demand for new chemicals spanning the fields of health care to materials science combined with the pressure to produce these substances in an environmentally benign fashion pose great challenges to the synthetic chemical community. The maximization of synthetic efficiency by the conversion of simple building blocks into complex targets remains a fundamental goal. In this context, ruthenium complexes catalyze a number of non-metathesis conversions and allow the rapid assembly of complex molecules with high selectivity and atom economy. These complexes often exhibit unusual reactivity. Careful consideration of the mechanistic underpinnings of the transformations can lead to the design of new reactions and the discovery of new reactivity.

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“…Based on this type of mechanism, dimerization of propargylic alcohols in the presence of water was described in 2001. [15] This reaction afforded α,β,γ,δunsaturated ketones in excellent yields with good selectivity. The postulated mechanism is the following: the [CpRu] coordinates two molecules of propargylic alcohol by oxidative coupling to afford the ruthenacyclopentadiene A.…”

Section: [Cpru]-catalyzed Alkyne-alkyne Coupling Reactionsmentioning

confidence: 94%

From Ruthenium to Copper: A la carte Tools for the Synthesis of Molecules of Interest

Monnier

Taillefer

2016

Chimia

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Well-defined ruthenium complexes and simple copper-ligand systems proved to be powerful catalysts for the construction of complex molecules from simple and abundant organic sources. In this account, chosen examples of reactions involving C-C bond formation catalyzed by [Ru(η(5)-C(5)H(5))-(CH(3)CN)(3)][PF(6)] will be presented. A practical synthesis of the versatile catalyst [Ru(η(5)-C(5)H(5))-(CH(3)CN)(3)][PF(6)] is also described via a simple and easy-handled procedure discovered in Geneva ten years ago. The second part of this review is focused on methodologies catalyzed by an association of a copper salt and a simple ligand for the formation of C-N, C-O and C-C bonds developed in our group in Montpellier. A brief overview of applications in life sciences and materials will conclude this article.

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An Unusual Ruthenium-Catalyzed Dimerization of Propargyl Alcohols

Abstract: Metal-catalyzed dimerizations of terminal alkynes have been extensively explored with numerous different metals. [1][2][3] Typically, the products are enynes derived from tail-to-tail or head-to-tail

Cited by 42 publications

References 6 publications

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

From Ruthenium to Copper: A la carte Tools for the Synthesis of Molecules of Interest

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