Utilization of potassium vinyltrifluoroborate in the development of a 1,2-dianion equivalent.
Previous studies of orthogonally reactive dibora species led to the discovery of a unique reactivity pattern associated with potassium vinyltrifluoroborate. Upon hydroboration, the vinyltrifluoroborate generates a 1,2-diboraethane, which is distinct from the 1,1-dibora intermediates generated when traditional alkenyldialkylboron species undergo hydroboration. The 1,2-dianion equivalent thus generated can be envisioned as a building block for the linkage of two different electrophiles via palladium-catalyzed Suzuki-Miyaura cross-couplings.
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Gary A
GA
Molander
Deidre L
DL
Sandrock
D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*
D001896:Boron Compounds; D009942:Organometallic Compounds; C541327:potassium vinyltrifluoroborate; D011188:Potassium