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- Title
Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.
- Authors
Thornbury, Richard T.; Toste, F. Dean
- Abstract
The palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids is described. Broad functional-group tolerance arises from a redox-neutral process by a palladium(II) active species which is proposed to undergo a β-fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (≥50:1) in all cases, and it is critical, as traditional chromatographic techniques often fail to separate monofluoroalkene isomers. As a demonstration of this method's unique combination of reactivity and functional-group tolerance, a Gleevec® analogue, using a monofluorostilbene as an amide isostere, was synthesized.
- Subjects
PALLADIUM catalysts; FUNCTIONAL groups; PALLADIUM; CHROMATOGRAPHIC analysis; STEREOSELECTIVE reactions; BORONIC acids; NONCARBOXYLIC acids
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 38, p11801
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201605651