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Friday, February 3, 2012

Recent advances in transition-metal-free carbon–carbon and carbon–heteroatom bond-forming reactions using arynes

Graphical abstract: Recent advances in transition-metal-free carbon–carbon and carbon–heteroatom bond-forming reactions using arynes

Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates

Graphical abstract: Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates

This comprehensive tutorial review focuses on well-defined cobalt complexes that serve as homogeneous catalysts for the production of polycarbonates and cyclic carbonates from the coupling of carbon dioxide and epoxides. Special considerations are given to the mechanistic pathways involved in these processes.

Green chemistry oriented organic synthesis in water


The use of water as solvent features many benefits such as improving reactivities and selectivities, simplifying the workup procedures, enabling the recycling of the catalyst and allowing mild reaction conditions and protecting-group free synthesis in addition to being benign itself. In addition, exploring organic chemistry in water can lead to uncommon reactivities and selectivities complementing the organic chemists' synthetic toolbox in organic solvents. Studying chemistry in water also allows insight to be gained into Nature's way of chemical synthesis. However, using water as solvent is not always green. This tutorial reviewbriefly discusses organic synthesis in water with a Green Chemistry perspective.

Graphical abstract: Green chemistry oriented organic synthesis in water

Thursday, February 2, 2012

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation

Graphical abstract: Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation

1-Benzyl ethers of (E)- and (Z)-hex-3-en-1,6-diols and hept-3-en-1,7-diols undergo a smooth oxidative cyclization with DDQ in the presence of In(OTf)3 through a sequential C–H bond activation and an intramolecular Prins cyclization to afford the corresponding trans- and cis-fused hexahydro-2H-furo[3,2-c]pyrans and octahydropyrano[4,3-b]pyrans respectively in good yields with an excellent stereoselectivity. Aryl tethered homoallylbenzyl ethers such as benzyl ethers of (E)- and (Z)-6-arylhex-3-enyl alcohols undergo a tandem Prins/Friedel–Crafts cyclization in the presence of stoichiometric amounts of DDQ and SnCl4via the benzylic C–H bond activation to furnish the corresponding trans- and cis-fused hexahydro-1H-benzo[f]isochromenes in good yields with complete stereoselectivity.

The Triple Role of Fluoride Ions in Palladium-Catalyzed Suzuki–Miyaura Reactions: Unprecedented Transmetalation from [ArPdFL2] Complexes

Direct Titanium-Mediated Conversion of Ketones into Enamides with Ammonia and Acetic Anhydride

Tuesday, January 31, 2012

Tuning the Regioselectivity of Palladium-Catalyzed Direct Arylation of Azoles by Metal Coordination

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Cationic Ruthenium(II) Catalysts for Oxidative C–H/N–H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water

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Synthesis of Indolo [1,2-a]Quinoxalines via a Pd-Catalyzed Regioselective C–H Olefination/Cyclization Sequence

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Ruthenium-Catalyzed Oxidative C–H Bond Olefination of N-Methoxybenzamides Using an Oxidizing Directing Group

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Tandem Rh(III)-Catalyzed Oxidative Acylation of Secondary Benzamides with Aldehydes and Intramolecular Cyclization: The Direct Synthesis of 3-Hydroxyisoindolin-1-ones

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Ruthenium-Catalyzed Oxidative C–H Alkenylations of Anilides and Benzamides in Water

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Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C–H/O–H Bond Cleavages

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Iron-Catalyzed Regio- and Stereoselective Chlorosulfonylation of Terminal Alkynes with Aromatic Sulfonyl Chlorides

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Terminal alkynes react with aromatic sulfonyl chlorides in the presence of an iron(II) catalyst and a phosphine ligand to give (E)-β-chlorovinylsulfones with 100% regio- and stereoselectivity. Various functional groups, such as chloride, bromide, iodide, nitro, ketone, and aldehyde, are tolerated under the reaction conditions. Addition of tosyl chloride to a 1,6-enyne followed by radical 5-exo-trig cyclization gave an exocyclic alkenylsulfone.

Rhodium-Catalyzed Xanthone Formation from 2-Aryloxybenzaldehydes via Cross-Dehydrogenative Coupling (CDC)

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