Enol Phosphinates and Phosphonates: Practical Electrophiles for Cross-Coupling Strategies

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Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity

Qian Wang, Jieping Zhu, Mathias Mamboury

The palladium-catalyzed reaction of a-haloketones with isocyanides afforded -oxo-ketenimines through alpha-hydride elimination of the beta-oxo-imidoyl palladium intermediates. Reaction of these relatively stable alpha-oxo ketenimines with nucleophiles suc ...

Wiley-Blackwell2017

Access to Chiral Cyclopentane Scaffolds by Enantioselective Nickel-Catalyzed Annulations

Joachim Sven Ernst Ahlin

The cyclopentane scaffold has attracted much attention due to its ubiquity in numerous bioactive natural products such as prostaglandins and polyquinanes. However, despite a plethora of available procedures to access this motif, a lack of methods that riva ...

EPFL2016

Suzuki-Miyaura cross-coupling of non-activated alkyl halides catalyzed by well-defined nickel pincer complexes

Thomas Clément Di Franco

Metal-catalyzed cross-coupling reactions are powerful and widespread methods for the carbon-carbon bond formation. Among the electrophile partners, non-activated alkyl halides remain challenging substrates because of their reluctance towards oxidative addi ...

EPFL2016

Palladium-Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification

Jérôme Waser, Ugo Jonathan Orcel

Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium-catalyzed oxy-alkynylation, oxy-arylation, or oxy-vinylation of allylic amines. High regio- and ...

Wiley-Blackwell2015

Mild and Phosphine-Free Iron-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides with Alkynyl Grignard Reagents

Xile Hu, Chi Wai Cheung, Peng Ren

A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to af ...

American Chemical Society2014

Suzuki-Miyaura Cross-Coupling Reactions of Unactivated Alkyl Halides Catalyzed by a Nickel Pincer Complex

Xile Hu, Thomas Clément Di Franco, Nicolas Francis Michel Boutin

A nickel(II) pincer complex, [((N2N)-N-Me)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane rea ...

Georg Thieme Verlag2013

Synthesis of Indoles by Copper-Catalyzed Heteroannulation of o-Aminophenylboronic Acid Pinacol Esters with β-Keto Esters

Qian Wang, Jieping Zhu, Ala Bunescu

Copper-catalyzed coupling of ortho-aminophenylboronic acid pinacol esters with β-ketoesters afforded, under mild base-free oxidative conditions, 2,3-disubstituted indoles featuring a key Chan-Lam type carbon-carbon bond forming reaction. ...

Georg Thieme Verlag2012

New Acetylene Chemistry : Direct [alpha]-Alkynylation of Carbonyls with Ethynyl Benziodoxolones (EBX)

Davinia Fernández González

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

A Well-Defined Ni Pincer Catalyst for Cross Coupling of Non-Activated Alkyl Halides and Direct C-H Alkylation

Oleg Vechorkin

Carbon-carbon bond forming reactions are among the most important and useful methods for organic synthesis. During the last years, significant progress has been made in this field. Whereas many catalysts were developed for the coupling of aryl, alkenyl, an ...

EPFL2011

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