Palladium‐Catalyzed Synthesis of Functional Tetralins <i>via</i> Benzylic Activation

Liégault, Benoît; Renaud, Jean‐Luc; Bruneau, Christian

doi:10.1002/adsc.200600547

Cited by 6 publications

(5 citation statements)

References 64 publications

(16 reference statements)

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“…However, the cycloaddition is often utilized with electronically biased alkenes, and examples with unactivated alkynes have not been reported so far. In contrast, palladium‐catalyzed Diels–Alder type reactions of ortho ‐[(trimethylsilyl)methyl]benzyl carbonates10 and α,α′‐dichloro‐ ortho ‐xylenes11 with activated alkenes were demonstrated by Kuwano and Shige, and Renaud, Bruneau, and Liégault, respectively [Eq. (3)].…”

Section: Methodsmentioning

confidence: 99%

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

2014

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A formal [4+2] cycloaddition of α,α′‐dichloro‐ortho‐xylenes with various alkynes has been developed using a low‐valent cobalt catalyst. The transformation has a wide substrate scope and high functional‐group tolerance and led to 1,4‐dihydronaphthalenes. The formed cycloadducts were easily aromatized with MnO2 under air. A mechanistic investigation suggests that the transformation proceeds through a benzyl cobaltation of alkyne, not the classical Diels–Alder reaction of ortho‐quinodimethanes. This methodology provides a straightforward and streamlined access to linearly expanded π‐conjugated aromatics.

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Section: Methodsmentioning

confidence: 99%

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

2014

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“…O rtho ‐substituted benzyl electrophiles have emerged as a means to generate similar products by palladium catalysis. Initial work by Bruneau reacted bis‐benzylic chloride 276 with polarized olefin acceptors such as 277 in the presence of catalytic palladium 135. Bruneau proposed that initial Heck‐type addition to the enoate occurred, followed by displacement of the second chloride with resultant palladium enolate 278 to furnish tetralin 279 (Scheme ).…”

Section: Palladiummentioning

confidence: 99%

In Situ Powder Diffraction Studies of Electrode Materials in Rechargeable Batteries

et al. 2015

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The ability to directly track the charge carrier in a battery as it inserts/extracts from an electrode during charge/discharge provides unparalleled insight for researchers into the working mechanism of the device. This crystallographic-electrochemical information can be used to design new materials or modify electrochemical conditions to improve battery performance characteristics, such as lifetime. Critical to collecting operando data used to obtain such information insitu while a battery functions are X-ray and neutron diffractometers with sufficient spatial and temporal resolution to capture complex and subtle structural changes. The number of operando battery experiments has dramatically increased in recent years, particularly those involving neutron powder diffraction. Herein, the importance of structure-property relationships to understanding battery function, why insitu experimentation is critical to this, and the types of experiments and electrochemical cells required to obtain such information are described. For each battery type, selected research that showcases the power of insitu and operando diffraction experiments to understand battery function is highlighted and future opportunities for such experiments are discussed. The intention is to encourage researchers to use insitu and operando techniques and to provide a concise overview of this area of research.Keywords situ, batteries, diffraction, studies, powder, electrode, materials, rechargeable Disciplines Engineering | Science and Technology Studies Publication DetailsSharma, N., Pang, W. Kong., Guo, Z. & Peterson, V. K. (2015). In situ powder diffraction studies of electrode materials in rechargeable batteries. ChemSusChem: chemistry and sustainability, energy and materials, 8 (17), 2826-2853. This journal article is available at Research Online: http://ro.uow.edu.au/eispapers/4279 In Situ Powder Diffraction Studies of Electrode Materials in Rechargeable BatteriesNeerajS harma,* [a] Wei Kong Pang, [b, c] Zaiping Guo, [c] and Vanessa K. Peterson [b] ChemSusChem 2015, 8,2826 -2853 2 015 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim 2826 Reviews DOI:1 0.1002/cssc.201500152 Batteries and Energy StorageIncreasingw orldwide need for energy is depleting our main energy sources, including fossil fuels such as coal, petroleum, and natural gas. Concurrently,t he combustion of fossil fuels is increasing harmful greenhouse gas emissionsa nd other environmentalp ollutants. Renewable ands ustainable energy is required to solve such problems. To enabler enewable energy, energy conversion and storage systems are essential to smooth out the intermittent nature of generation. There are an umber of energy-conversion and storage systems (e.g.,f lywheels), but lithium-ion rechargeable batteries are proving to be the dominantr echargeableb attery system. This is because of their high energy density,h igh power density,a nd higher operating voltage comparedw ith other rechargeable batteries, such as lead-acid and widely used nickel-metal-hybrid batteri...

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“…Erste Arbeiten durch Bruneau et al. betrafen die Umsetzung des Bisbenzylchlorids 276 mit polarisierten Alkenakzeptoren wie 277 in Gegenwart eines Palladiumkatalysators 135. Bruneau vermutete, dass zunächst eine Heck‐Addition an das Enolat stattfindet und danach das zweite Chlorid durch das entstandene Palladiumenolat 278 unter Bildung des Tetralins 279 ausgetauscht wird (Schema ).…”

Section: Palladiumunclassified

Struktur und Reaktivität später Übergangsmetall‐ η³‐Benzylkomplexe

Trost

Czabaniuk

2014

Angewandte Chemie

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Die Koordination von Übergangsmetallen an organische Einheiten kann zu Komplexen mit faszinierenden und unerwarteten Bindungsmustern führen. Untersuchungen von Benzylmetall‐Komplexen haben die Möglichkeit einer η3‐Koordination ergeben, die zu einem desaromatisierten Ring führt. Als Zwischenstufen in Katalysezyklen bieten diese Komplexe zudem Einblicke in Reaktionsmechanismen. In diesem Aufsatz werden die Synthese und Charakterisierung dieser Komplexe mit späten Übergangsmetallen sowie die nachfolgende Entwicklung katalytischer Methoden zur Funktionalisierung der Benzylposition einschließlich asymmetrischer Varianten besprochen.

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Palladium‐Catalyzed Synthesis of Functional Tetralins via Benzylic Activation

Cited by 6 publications

References 64 publications

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

In Situ Powder Diffraction Studies of Electrode Materials in Rechargeable Batteries

Struktur und Reaktivität später Übergangsmetall‐ η³‐Benzylkomplexe

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Palladium‐Catalyzed Synthesis of Functional Tetralins via Benzylic Activation

Cited by 6 publications

References 64 publications

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

Cobalt‐Catalyzed Formal [4+2] Cycloaddition of α,α′‐Dichloro‐ortho‐Xylenes with Alkynes

In Situ Powder Diffraction Studies of Electrode Materials in Rechargeable Batteries

Struktur und Reaktivität später Übergangsmetall‐ η3‐Benzylkomplexe

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Struktur und Reaktivität später Übergangsmetall‐ η³‐Benzylkomplexe