A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds

Authors

  • Zhonglin Liu The Scripps Research Institute - United States ,
  • Lucas Oxtoby The Scripps Research Institute - United States ,
  • Zi-Qi Li The Scripps Research Institute - United States ,
  • Nana Kim The Scripps Research Institute - United States ,
  • Geraint Davies Bristol Myers Squibb - United States ,
  • Keary Engle The Scripps Research Institute - United States

Abstract

The site-selective palladium-catalyzed three-component coupling of unactivated alkenyl carbonyl compounds, aryl- or alkenylboronic acids, and N-fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary is proposed to facilitate challenging C(sp3)–F reductive elimination from a Pd(IV) intermediate to afford 1,2-carbofluorination products in good yields and with high regioselectivity.

Content

Supplementary material

Supporting Info
experimental procedures, characterization data for new compounds, copies of NMR spectra, and X-ray crystal structure data
CIF_S-3
crystallographic information file for compound S-3