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Palladium-Catalyzed Domino Intramolecular N-Arylation/Intermolecular C-C Bond Formation for the Synthesis of Functionalized Benzodiazepinediones

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Total Synthesis of Cyrneine A

Karl Gademann, Cindy Fellay

The tricyclic diterpene cyrneine A featuring a hexatrienal unit was prepared synthetically for the first time by a Heck reaction, a carbene ring expansion, and a reductive carbonylation. The structure of the natural product was assigned by X‐ray crystal an ...

2012

This thesis is divided in seven main chapters including an introduction about the state of the art in the field, four main chapters describing the main part of the work, a short insight on the implications of the presented results for other research projec ...

EPFL2011

Palladium Alkynyl and Allenylidene Complexes: Very Efficient Precatalysts for C-C Coupling Reactions

Oxidative addition of BrC CC(=O)O-menthyl (1a) to [Pd(PPh3)(4)] affords the alkynyl complex trans-[Br(PPh3)(2)Pd-C CC(=O)O-menthyl] (2a). Subsequent reaction of 2a with trifluoroacetate gives trans-[(F3CCOO)(PPh3)(2)Pd-C CC(=O)O-menthyl] (3a). Reaction of ...

2011

Protecting-Group-Free Total Synthesis of (E) and (Z)-Alstoscholarine

Jieping Zhu

Looking for hidden symmetry: The first asymmetric total synthesis of pentacyclic (E)- and (Z)-alstoscholarines is accomplished starting from cyclic meso-anhydride 9. The absolute configuration was set by an organocatalytic desymmetrization of 9. Other key ...

Wiley-Blackwell2011

Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles

Jieping Zhu

A palladium-catalyzed oxidative carbo-heterofunctionalization of aniline derivs. involving concomitant direct C-H functionalization and C-X bond formation was developed. By simply changing the reaction conditions (solvent and catalyst), either 3,3'-disubst ...

2010

The reaction of U(III) with Schiff base ligands and the reduction of U(IV) Schiff base complexes both promote C-C bond formation to afford dinuclear or mononuclear U(IV) amido complexes, which can release up to four electrons to substrates through the oxid ...

2010

Solvent-enhanced coupling of sterically hindered reagents and aryl chlorides using functionalized ionic liquids

Paul Joseph Dyson, Zhaofu Fei, Ning Yan, Yuehui Li, Xuemei Yang

A highly efficient and poison-resistant system for the Suzuki coupling reaction based on hydroxyl-functionalized ionic liq. solvents has been established. Coupling of RC6H4X (X = Br, I, Cl) and 2-bromothiophene with R1C6H4B(OH)2 in 2-hydroxyethyl-substitut ...

2009

Iron-Catalyzed Mizoroki–Heck Cross-Coupling Reaction with Styrenes

Pierre Vogel, Chandra Mouleeswara Rao Volla, Rafal Loska

In the presence of iron(II) chloride (FeCl2 ; 20 mol%) and potassium tert-butoxide (t- BuOK; 4 equiv.) in dimethyl sulfoxide (DMSO), aryl and heteroaryl iodides undergo stereoselective Mizoroki–Heck C—C cross-coupling reactions with styrenes at 60 8C givin ...

2008

, , , , ,

Imidazolium- and pyridinium-based ionic liqs. with ether/polyether substituents have been evaluated as solvents for palladium-catalyzed Suzuki C-C coupling reactions. In general, reactions proceed more efficiently in these solvents compared to other ionic ...

2008

, ,

Two new aminophosphines, benzyl-N(Ph2P)(2) and 2-picolyl-N(Ph2P)(2), have been synthesized. Oxidation of the aminophosphines with either hydrogen peroxide, elemental sulfur and selenium gave the corresponding oxides, sulfides and selenides benzyl-N(Ph2P=E) ...

2008