Categories: C-H Bond Formation >
Protodeboronations
Recent Literature
A concise and practical protodeboronation of arylboronic acids works under mild conditions in aqueous NaClO at 100°C. The strategy
is low-cost, transition-metal-free, and base-free.
M. Li, Y. Tang, J. Gao, G. Rao, Z. Mao, Synlett, 2020,
31,
2039-2042.
A mild gold-catalyzed protodeboronation reaction can be carried out in green
solvents without any acid or base additives. Therefore, the reaction is very
functional-group-tolerant and enables the use of the boronic acid group as an
effective traceless directing or blocking group.
G. Barker, S. Webster, D. G. Johnson, R. Curley, M. Andrews, P. C. Young, S. A.
Macgregor, A.-L. Lee, J. Org. Chem.,
2015,
80, 9807-9816.
CsF with 1.1 equiv of H2O effects highly efficient
protodeboronation on tertiary diarylalkyl boronic esters with essentially
complete retention of configuration, whereas TBAFˇ3H2O can be used
for tertiary aryldialkyl boronic esters. Furthermore, substituting D2O
for H2O provides ready access to deuterium-labeled enantioenriched
tertiary alkanes. A short synthesis of the sesquiterpene (S)-turmerone is
described.
S. Nave, R. P. Sonawane, T. G. Elford, V. K. Aggarwal, J. Am. Chem. Soc., 2010,
132, 17096-17098.
A neighboring boronate group in vicinal bis(boronic esters) provides a
dramatic rate acceleration in transmetalation to copper and thereby enables
unprecedented site-selective cross-couplings allyl, alkynyl, and propargyl
electrophiles as well as a simple proton. This cross-coupling operates under
practical experimental conditions.
N. Xu, Z. Kong, J. Z. Wang, G. J. Lovinger, J. P. Morken, J. Am. Chem. Soc.,
2022, 144, 17815-17823.