Publications by Runze Mao | EPFL Graph Search

Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp(3))-H Bonds and Aliphatic Carboxylic Acids

Intermolecular functionalization of C(sp(3))-H bonds and aliphatic carboxylic acids enables the efficient synthesis of high value-added organic compounds from readily available starting materials. Although methods involving hydrogen atom transfer have been ...

2021

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Xile Hu, Lara Lavrencic, Runze Mao, Xiangli Yi

Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carbox ...

Wiley-VCH Verlag GmbH2021

Tandem Photoredox and Copper-Catalyzed Decarboxylative C(sp3)–N Coupling of Anilines and Imines Using an Organic Photocatalyst

Xile Hu, Jérôme Waser, Runze Mao, Marion Marie-Agnès Garreau, Guido Barzanò

An organic photoredox catalyst, 4CzIPN, was used in combination with a copper catalyst, CuCl, to effect decarboxylative C(sp3)–N coupling. The coupling worked with both anilines and imines as nitrogen sources and could be used to prepare a variety of alkyl ...

2020

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

Aliphatic Carboxylic Acids as Coupling Partners in Carbon-Heteroatom Bond-Forming Reactions

Runze Mao

Carboxylic acids are one of the most suitable starting materials for synthesis. They are readily available and therefore inexpensive, stable and non-toxic. Many carboxylic acids can be obtained directly from natural resources, thus avoiding the extraction ...

EPFL2020

Deoxygenative trifluoromethylthiolation of carboxylic acids

Xile Hu, Runze Mao, Srikrishna Bera, Alexis Baptiste Cheseaux

Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an "umpolung" strategy where triphenylphosphine is used to first activate an electrop ...

2019

Decarboxylative C(sp3 )−O Cross-Coupling

Xile Hu, Runze Mao, Jonathan Balon

Alkyl aryl ethers are an important class of compounds in medicinal and agricultural chemistry. Catalytic C(sp3)−O cross‐coupling of alkyl electrophiles with phenols is an unexplored disconnection strategy to the synthesis of alkyl aryl ethers, with the pot ...

Wiley-VCH Verlag GmbH2018

Decarboxylative C(sp3)–N cross-coupling via synergetic photoredox and copper catalysis

Xile Hu, Runze Mao, Jonathan Balon, Adrian Frey

Amines are a quintessential moiety in bioactive molecules, pharmaceuticals and organic materials. Transition-metal-catalysed C–N coupling of aryl electrophiles has been established as a powerful and reliable method for amine synthesis. However, the analogo ...

2018

Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

Xile Hu, Runze Mao, Jonathan Balon

Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal‐catalyzed cross‐coupling of alkyl electrophiles with nitrogen nucleophiles. ...

Wiley-VCH Verlag GmbH2018