Publication
Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents
Related publications (56)
Anhydrous Conditions Enable the Catalyst-Free Carboxylation of Aromatic Alkynes with CO2 under Mild Conditions
Paul Joseph Dyson, Marinella Mazzanti, Felix Daniel Bobbink, Davide Toniolo
The direct carboxylation of aromatic alkynes with CO2, a cheap and widely available C1 source, is the most attractive method for the synthesis of carboxylic acids. Here we show that direct carboxylation of terminal alkynes can be simply performed in near-q ...
WILEY-V C H VERLAG GMBH2020Photoredox-Catalyzed Decarboxylation for the Transfer of Alkynes and Nitriles Using Hypervalent Iodine Reagents
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 ...
EPFL2019Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents
Jérôme Waser, Stefano Nicolai, Franck Le Vaillant, Stephanie Grace Elizabeth Amos, Alec Gagnebin
Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxo ...
2019Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
Jérôme Waser, Matthew Wodrich, Paola Caramenti, Romain Gaëtan Tessier, 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 ...
2019Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds
Jérôme Waser, Franck Le Vaillant
The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensivel ...
2019Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds
Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Lionel Schouwey, Verity Barber
Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first syn ...
2019Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes
Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...
EPFL2017Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation
Jérôme Waser, Matthew Wodrich, Franck Le Vaillant
The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and no ...
2017Indole- 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 ...
2017Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents
Jérôme Waser, Durga Prasada Rao Hari
Alkynes have found widespread applications in synthetic chemistry, biology, and materials sciences. In recent years, methods based on electrophilic alkynylation with hypervalent iodine reagents have made acetylene synthesis more flexible and efficient, but ...
American Chemical Society2016