title: Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.
abstract: The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.
authors.forename: Kai
authors.initials: K
authors.lastname: Hong
authors.forename: Xun
authors.initials: X
authors.lastname: Liu
authors.forename: James P
authors.initials: JP
authors.lastname: Morken
mesh_terms: D000478:Alkylation; D000838:Anions / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D003500:Cyclization; D004952:Esters; D008670:Metals / Q000737:chemistry; D010087:Oxides / Q000737:chemistry
chemical_list: D000838:Anions; D001897:Boronic Acids; D004952:Esters; D008670:Metals; D010087:Oxides