Publications related to Hydrocyanation

Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Jérôme Waser, Matthew Wodrich, André Bossonnet

We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

2023

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Chao Fan, Srikrishna Bera

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

2022

Novel cationic 1,2,4-selenadiazoles: synthesis via addition of 2-pyridylselenyl halides to unactivated nitriles, structures and four-center SeMIDLINE HORIZONTAL ELLIPSISN contacts

Euro Solari, Alexander Tskhovrebov

2-Pyridylselenyl halides undergo facile coupling with a triple CN bond of unactivated nitriles. Unprecedented heterocyclization allowed the preparation of a novel class of cationic 1,2,4-selenadiazoles in remarkably high yields. Cationic 1,2,4-selenadiazol ...

ROYAL SOC CHEMISTRY2021

Intermolecular oxidative amination of unactivated alkenes by dual photoredox and copper catalysis

Xile Hu, Xiangli Yi

Oxidative amination of alkenes via amidyl radical addition is potentially an efficient method to generate allylic amines, which are versatile synthetic intermediates to bioactive compounds and organic materials. Here by combining photochemical generation o ...

ROYAL SOC CHEMISTRY2021

Developing the Catalytic Applications of 1,3,2-Diazaphospholenes

John Henry Reed

The development of new catalytic methods for organic synthesis is a critical endeavour in order to obviate the economic and ecological drawbacks of stoichiometric organic synthesis. While catalysis can offer significant advantages in terms of atom-economy, ...

EPFL2021

Propelling the hydrogen economy: from chemical storage and delivery to utilization in biomass conversion

Lu Chen

Since H2 is a non-polluting, inexhaustible, efficient, and sustainable energy carrier, it has been forecast to become one of the major carriers of energy in the future and is also essential in the production of feedstock chemicals derived from renewable ca ...

EPFL2021

Operando diffuse reflectance infrared detection of cyanide intermediate species during the reaction of formaldehyde with ammonia over V2O(5)/ WO3-TiO2

Oliver Kröcher, Davide Ferri, Rob Jeremiah G. Nuguid

Hydrogen cyanide (HCN) is a highly poisonous gas that can form through the reaction between formaldehyde and ammonia (NH3) in the exhaust. While this detrimental side reaction has been the subject of recent catalytic studies under selective catalytic reduc ...

ELSEVIER2021

Copper-Catalyzed Cyanoalkylative Aziridination of N-Sulfonyl Allylamines

Qian Wang, Jieping Zhu, Minh Tu Ha, Weisi Guo

Reaction of N-arylsulfonyl allylamines with alkyl nitriles in the presence of di-tert-butyl peroxide (DTBP) and a catalytic amount of copper salt afforded homologated aziridines in 43-86% yield. A sequence involving addition of the in situ generated cyanom ...

Wiley2020

Enantioselective C(sp(3))-C(sp(3)) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis

Xile Hu, Runze Mao, Srikrishna Bera

Cross-coupling of two alkyl fragments is an efficient method to produce organic molecules rich in sp(3)-hybridized carbon centres, which are attractive candidate compounds in drug discovery. Enantioselective C(sp(3))-C(sp(3)) coupling is challenging, espec ...

2020

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

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

Dual Photoredox/Copper Catalysis for the Remote C(sp3 )−H Functionalization of Alcohols and Alkyl Halides by N -Alkoxypyridinium Salts

Qian Wang, Xu Bao, Jieping Zhu

Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded d-azido, d-cyano, and d-thiocyanato alcohols in high yields. The reaction went through a domino proc ...

Wiley-VCH Verlag GmbH2019

Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis

Xile Hu, Xiangli Yi

In oxidative electrochemical organic synthesis, radical intermediates are often oxidized to cations on the way to final product formation. Herein, we describe an approach to transform electrochemically generated organic radical intermediates into neutral p ...

Wiley-VCH Verlag GmbH2019

Photoredox-Catalyzed Decarboxylation for the Transfer of Alkynes and Nitriles Using Hypervalent Iodine Reagents

Franck Le Vaillant

Aliphatic alkynes and nitriles are privileged motifs in organic chemistry. Therefore, alkynes and nitriles have played a central role for the exploration and development of novel strategies to forge C-C bonds in efficient manner. They are broadly used as v ...

EPFL2019

Total Synthesis of Alstilobanine C, Undulifoline and Alstilobanine B

Nicolas David Gaeng

The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis. Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...

EPFL2018

Laboratory testing of gas shales in unsaturated conditions

Lyesse Laloui, Alessio Ferrari, Alberto Minardi

Water uptake of gas shales is commonly considered one of the most important factors responsible for fluid loss during flowback operations after hydraulic fracturing. Imbibition experiments cover a key role in this context to analyze the impact of several f ...

2018

In situ tether formation from amines and alcohols enabling highly selective Tsuji-Trost allylation and olefin functionalization

Jérôme Waser, Ugo Jonathan Orcel

The use of tethers allows to overcome reactivity and selectivity issues often encountered with intermolecular reactions. Although tethers have been successfully applied for decades, their installation and removal usually requires additional steps. This min ...

2017

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

Xile Hu, Ivan Buslov, Fang Song

The first efficient and non-precious nanoparticle catalyst for alkene hydrosilylation with commercially relevant tertiary silanes has been developed. The nickel nanoparticle catalyst was prepared in situ from a simple nickel alkoxide precatalyst Ni((OBu)-B ...

Wiley-Blackwell2016

Enantioselective Synthesis of Quaternary α-Amino Acids Enabled by the Versatility of the Phenylselenonyl Group

Qian Wang, Jieping Zhu, Antonin François Roland Clemenceau

A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of alpha-alkyl substituted alpha-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched alpha,alpha-dialkyl substituted alpha-nitroacetates were subsequen ...

Wiley-Blackwell2016

Rh(III)-Catalyzed C-H Functionalizations as Strategies for Versatile Organic Building Blocks

Van Manh Pham

Transition-metal catalyzed C-H functionalizations have impacted and changed synthetic approaches towards the construction of relevant complex molecules, comprising natural products, active pharmaceutical ingredients, and organic materials. This thesis desc ...

EPFL2016

Elastomers with tunable dielectric and electromechanical properties

Frank Nüesch

Novel electroresponsive silicone elastomers modified with nitrile groups are presented, whose dielectric permittivity (epsilon') is tuned from epsilon' = 4.3 to epsilon' = 17.4. They are prepared in a one-step process starting from a high molecular weight ...

Royal Society of Chemistry2016