Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 38, Pages 11620-11623Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706798
Keywords
allenes; halogenation; hypervalent compounds; rearrangement; synthetic methods
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Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- University of Waterloo
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Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo) toluene in the presence of 20 mol% BF3 center dot OEt2 to yield alpha-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene pi bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and alpha-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.
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