Jerome Waser Group – Professor Product Portal

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Professor Jérôme Waser

The Waser laboratory is working on the development of non-conventional bond disconnections using the unique properties of hypervalent iodine reagents. In particular, they discovered the exceptional properties of 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) for electrophilic alkynylation. First synthesized by Zhdankin and co-workers in 1996 (J. Org. Chem 1996, 61, 6547), the synthetic potential of this reagent remained unexploited until the Waser group reported its use for the gold-catalyzed direct alkynylation of electron-rich aromatic compounds, such as indoles, thiophenes or anilines. TIPS-EBX was also the reagent of choice for the palladium-catalyzed oxy- and amino-alkynylation of olefins. Finally, this reagent can also be used for the direct alkynylation of keto esters and thiols or radical decarboxylative alkynylation. TIPS-EBX is a bench-stable, crystalline compound, which makes it particularly user friendly. The Waser laboratory is currently continuing its work on the development of hypervalent iodine reagents for the transfer of acetylenes and other functional groups.

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Reto Frei, Jérôme Waser
Journal of the American Chemical Society, 135(26), 9620-9623 (2013)
A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available...Read More
Stefano Nicolai et. al
Organic Letters, 12(2), 384-387 (2009)
The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room tempe...Read More
Jonathan P Brand et. al
Angewandte Chemie (International Edition), 48(49), 9346-9349 (2009)