Catalysis

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

Thumbnail image of Manuscript.pdf

Supplementary material

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