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- Title
Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α-(Difluoromethyl)styrenes.
- Authors
Zhao, Zhensheng; Racicot, Léanne; Murphy, Graham K.
- Abstract
Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3⋅OEt2 to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.
- Subjects
STYRENE; BENZENE compound synthesis; REARRANGEMENTS (Chemistry); ALLENE; TOLUENE; FLUORINATION
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 38, p11778
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201706798