Bromo-boronolactonization of olefins.
Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/H(2)O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.
Falck
J R
JR
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390-9038, USA. j.flack@utsouthwestern.edu
Bondlela
M
M
Venkataraman
S K
SK
Srinivas
D
D
D000475:Alkenes / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*
D000475:Alkenes; D001896:Boron Compounds; D001897:Boronic Acids; D007783:Lactones