Publications associées à Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

Construction of Functional Superhydrophobic Biochars as Hydrogen Transfer Catalysts for Dehydrogenation of N-Heterocycles

Feng Zhou, Zhaowen Dong

To endow metal-free materials with the high catalytic activity that is typically featured by a metal-based catalyst is yet a constant pursuit in the field of catalytic chemistry. In this work, novel functional biochars (DCNs) were prepared from wheat straw ...

AMER CHEMICAL SOC2021

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Acceptorless dehydrogenation and hydrogenation of N- and O-containing compounds on Pd3Au1(111) facets

Paul Joseph Dyson, Zhaofu Fei, Antoine Philippe Van Muyden, Tao Wang, Zhangjun Huang, Xinjiang Cui

Catalytic dehydrogenation and hydrogenation of amines and alcohols are important in the synthesis of fine chemicals. Despite several efficient homogeneous catalysts having been identified, highly active heterogeneous catalysts remain elusive, although they ...

2020

Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Nicolai Cramer, Daria Grosheva

Asymmetric metal-catalyzed C-H functionalization is a powerful strategy for the rapid generation of complex target molecules from simple precursors. While aryl (pseudo) halides have been used as electrophilic substrates in enantioselective Pd(0)-catalyzed ...

2019

Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Daria Grosheva

Asymmetric metal-catalyzed C-H functionalization has enjoyed great success as a powerful strategy for the rapid construction of elaborate structures from simple precursors. For example, aryl (pseudo)halides have been extensively employed as electrophilic s ...

EPFL2019

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Paul Joseph Dyson, Martin Hulla, Simon Nussbaum, Alexy Robert Bonnin

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...

Royal Society of Chemistry2019

Developing Reactions of Strained Rings : Enantioselective Desymmetrization of meso-Diaminocyclopropanes and Annulation of Donor-Acceptor Aminocyclobutanes

Daniele Perrotta

Carbo- and heterocyclic structures containing nitrogen-substituted stereocenters are recurrent structural motifs in natural and bioactive compounds, therefore constituting a privileged class of synthetic targets. In this regard, substituted three- and four ...

EPFL2018

In Situ Tethering Strategies for the 3-Component Synthesis of Vicinal Amino Alcohols and Diamines via Pd-Catalyzed Carboetherification and Carboamination

Ugo Jonathan Orcel

Vicinal amino alcohols and diamines are privileged motifs in organic chemistry. As such, they have been targets of choice for exploring and developing novel and more efficient strategies in organic synthesis. In this context, the difunctionalization of ole ...

EPFL2017

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

Solvent effects in catalysis: rational improvements of catalysts via manipulation of solvent interactions

Paul Joseph Dyson, Philip Gregory Jessop

In homogeneous catalysis, the main emphasis on improving catalyst performance (rate, yield and selectivity) is directed towards manipulation of the ligands. The steric and electronic effects of ligands are extremely well understood and the rational design ...

2016

Lewis acid Catalyzed Annulations of Donor-Acceptor Aminocyclopropanes and Aminocyclobutanes

Sophie Lucie Racine

Organic molecules are indispensable have greatly contributed to the confort of our modern life. Nevertheless, humanity is facing now new challenges such as environmental issues and emerging drug resistances. In order to solve these major concerns, chemists ...

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

On-Surface Assembly and Reactions of Organic Molecules in Ultra-High Vacuum

Claudius Morchutt

This thesis comprises the study of two types of 2D materials, those stabilized by non-covalent and those by covalent interactions. They are synthesized and studied on well-defined metallic surfaces in ultra-high vacuum (UHV). The self-assembly of terephtha ...

EPFL2016

Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals

Nicolai Cramer, Laetitia Marie Mélanie Souillart

Selective cleavages of carbon-carbon bonds catalyzed by transition-metal complexes have been shown to be increasingly versatile tools for organic synthesis allowing for complementary synthetic strategies. Numerous examples of transition-metal catalyzed C-C ...

Amer Chemical Soc2015

Chiral gamma-Lactams by Enantioselective Palladium(0)-Catalyzed Cyclopropane Functionalizations

Nicolai Cramer, Julia Pedroni

Cyclopropanes fused to pyrrolidines are important structural features found in a number of marketed drugs and development candidates. Typically, their synthesis involves the cyclopropanation of a dihydropyrrole precursor. Reported herein is a complementary ...

Wiley-VCH Verlag GmbH2015

Access to beta-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp(3))-H Alkylation

Tanguy Jean Daniel Saget, Nicolai Cramer, Michele Boghi, Julia Pedroni

beta-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transitionmetal- catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon ...

Wiley-Blackwell2014

Enantioselective palladium(0)-catalyzed C-H arylation strategy for chiral heterocycles

Tanguy Jean Daniel Saget, Nicolai Cramer

Transition-metal-catalyzed C-H functionalizations have emerged as complementary and powerful tools to access molecular complexity from widely available starting materials. Herein, we present a strategy for asymmetric intramolecular Pd(0)-catalyzed C-H func ...

De Gruyter2014

Catalytic Formal Homo-Nazarov Reaction and Other Cyclizations of Cyclopropanes : from Methodology to Total Synthesis

Filippo De Simone

The increasing progress in medicinal chemistry and chemical biology requires more versatile synthetic strategies for the generation of libraries of active compounds and theirs analogues. A wide range of biologically active natural and synthetic compounds c ...

EPFL2012

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