Publications by Paola Caramenti

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Matthew Wodrich, Jérôme Waser, Romain Gaëtan Tessier, Paola Caramenti, Nina Declas

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability

Jérôme Waser, Stefano Nicolai, Lionel Schouwey, Durga Prasada Rao Hari, Paola Caramenti, Miyeon Chang

The hypervalent iodine reagent 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step fr ...

2019

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

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

Jérôme Waser, Paola Caramenti, Raj Kumar Nandi

2018

Cyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung

Jérôme Waser, Durga Prasada Rao Hari, Paola Caramenti

2018

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

Jérôme Waser, Paola Caramenti, Erwann Stefan Grenet, Ashis Kumar Das

2018

Bench-Stable Electrophilic Indole and Pyrrole Reagents: Serendipitous Discovery and Use in C–H Functionalization

Paola Caramenti

Wiley-VHCA AG2017

Gold-catalyzed domino cyclization-alkynylation reactions with EBX reagents: new insights into the reaction mechanism

Jérôme Waser, Yifan Li, Paola Caramenti

Gold-catalyzed domino processes constitute a useful alternative to C-H functionalization for the synthesis of functionalized (hetero)arenes. Herein, we report computational studies on the gold-catalyzed cyclization alkynylation of keto-allenes with ethynyl ...

2017

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

Jérôme Waser, Stefano Nicolai, Paola Caramenti

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 degrees C and were applied in the C-H arylation of unactivated arene ...

2017

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: alpha- or beta- pi-Addition?

Matthew Wodrich, Jérôme Waser, Paola Caramenti

The alkynylation of thiols with EthynylBenziodoXolone (EBX) reagents is a fast and chemoselective method for the synthesis of thioalkynes. Combined experimental and computational studies are reported, which led to the identification of a new mechanism for ...

2016

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Jérôme Waser, Maria Victoria Vita, Paola Caramenti

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladiumcatalyzed decarboxylative allylation of alpha-azido and cyano beta-ketoesters is reported. Indano ...

American Chemical Society2015