Direct vinylation and difluorovinylation of arylboronic acids using vinyl- and 2,2-difluorovinyl tosylates via the Suzuki-Miyaura cross coupling.
General reaction conditions were developed for the Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.
Gøgsig
Thomas M
TM
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Søbjerg
Lina S
LS
Lindhardt
Anders T
AT
Jensen
Kim L
KL
Skrydstrup
Troels
T
D001897:Boronic Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004583:Electrons; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020058:Styrene / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001897:Boronic Acids; D003432:Cross-Linking Reagents; D017611:Fluorine Compounds; D014105:Tosyl Compounds; D014753:Vinyl Compounds; D020058:Styrene