Palladium-Catalyzed Stereoselective Hydrodefluorination of Tetrasubstituted gem-Difluoroalkenes

A highly stereoselective palladium(0)-catalyzed hydrodefluorination (HDF) of tetrasubstituted gem-difluoroalkenes is developed. By using catalytic Pd­(PPh3)4 (2.5–5 mol %) and hydrosilane Me2PhSiH, various trisubstituted terminal (E)-monofluoroalkenes can be synthesized with excellent E/Z selectivit...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 22; no. 13; pp. 5193 - 5197
Main Authors Ma, Qiao, Liu, Caroline, Tsui, Gavin Chit
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
POLYFLUOROARENES
CONVERSION
REACTIVITY
FLUORO COMPLEX
FLUOROPYRIDINES
C-F
F BOND ACTIVATION
ACCESS
Online AccessGet full text

Cover

More Information
Summary:A highly stereoselective palladium(0)-catalyzed hydrodefluorination (HDF) of tetrasubstituted gem-difluoroalkenes is developed. By using catalytic Pd­(PPh3)4 (2.5–5 mol %) and hydrosilane Me2PhSiH, various trisubstituted terminal (E)-monofluoroalkenes can be synthesized with excellent E/Z selectivity (>99:1) and good functional group tolerability. The key stereocontrol should be exerted by an ester-directed C–F bond oxidative addition step in the catalytic cycle.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01813