Org Lett
Department of Chemistry and Chemical Biology , Harvard University, Cambridge , Massachusetts 02138 , United States.
Published: July 2019
The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluoride-bearing stereocenters. Selectivity for 1,2-difluorination versus a rearrangement pathway resulting in 1,1-difluorination is enforced through anchimeric assistance from a N- tert-butyl amide substituent.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7330813 | PMC |
http://dx.doi.org/10.1021/acs.orglett.9b00938 | DOI Listing |
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