Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts.
(E)- and (Z)-(fluoroalkenyl)boronates were prepared stereospecifically by the reaction of 2-fluoroalkylideneiodonium ylide generated from (E)- or (Z)-(2-fluoroalkenyl)iodonium salts with di(p-fluorophenoxy)alkylboranes, followed by transesterification to pinacol esters. The resulting pinacol esters of (fluoroalkenyl)boranes were used for the stereoselective synthesis of trisubstituted fluoroalkenes by cross-coupling reactions.
Guan
Tong
T
Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Yoshida
Masanori
M
Hara
Shoji
S
D000475:Alkenes / Q000737:chemistry*; D001881:Borates; D001888:Boric Acids / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D001881:Borates; D001888:Boric Acids; D001897:Boronic Acids; D009861:Onium Compounds; D012492:Salts; D007455:Iodine; C098759:fluoroboric acid