Chemodivergent Csp 3 ─F bond functionalization and cross-electrophile alkyl-alkyl coupling with alkyl fluorides

• DOI: 10.1126/sciadv.abn7819
• Publication Date: 2022-05-27T17:58:42Z
• Authors: Kaluvu Balaraman; Christian Wolf
• Keywords: Surface Modification

The widespread use of fluorinated organic compounds in the health, agrochemical, and materials sciences is sustained by a steadily growing pool commercially available fine chemicals. synthetic utility increasingly ubiquitous Csp 3 ─F bond, however, remains to be fully exploited, which often difficult task because its paramount stability chemical inertness. Here, we demonstrate chemodivergent activation monofluoroalkyl toward either nucleophilic or electrophilic intermediates. This accomplished under conditions that are compatible with several reaction types many functional groups, drastically widens current scope organofluorine chemistry sets stage for carbon-carbon carbon-heteroatom bond formations, stereoselective construction bisoxindole alkaloid scaffolds via situ Umpolung, cross-electrophilic coupling methodology. selective generation species possibility doing so simultaneously or, alternatively, switching molecular polarity enable previously unidentified opportunities recognize alkyl fluorides as building blocks.