title: A general method for interconversion of boronic acid protecting groups: trifluoroborates as common intermediates.
abstract: We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.
authors.affiliation: †School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.|‡CSIRO Materials Science and Engineering, Clayton, VIC 3168, Australia.
authors.forename: Quentin I
authors.initials: QI
authors.lastname: Churches
authors.affiliation: †School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
authors.forename: Joel F
authors.initials: JF
authors.lastname: Hooper
authors.affiliation: †School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
authors.forename: Craig A
authors.initials: CA
authors.lastname: Hutton