Categories: C-B Bond Formation > Synthesis of boronic acids and boronates >
Synthesis of benzylboronic acids and benzylboronates
Recent Literature
A catalytic amount of Mg as the only metal enables a reductive coupling between
benzyl halides and pinacolborane. HBpin acts both as an electrophile and as a
reducing agent to regenerate an organomagnesium species in situ. An hydride
oxidation mechanism is proposed on the basis of DFT calculations.
C. Pintaric, S. Olivero, Y. Gimbert, P. Y. Chavant, E. Duņach, J. Am. Chem. Soc., 2010,
132, 11825-11827.
A regioselective hydroboration of vinylarenes catalyzed by a Rh(I)-DPPB complex
proceeded rapidly when DMAP was used as an additive to furnish the desired
boronates in good to excellent yield with high regioselectivity.
K. Endo, M. Hirokami, K. Takeuchi, T. Shibata, Synlett, 2008,
3231-3233.
CsF with 1.1 equiv of H2O effects highly efficient
protodeboronation on tertiary diarylalkyl boronic esters with essentially
complete retention of configuration, whereas TBAF·3H2O 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.
Related
The use of an equimolar amount of base with a diborylmethane enabled a
chemoselective Pd-catalyzed Suzuki–Miyaura cross-coupling reaction for the
synthesis of various benzylboronate derivatives in very good yields. Reactions
of sterically hindered aryl bromides can give products in good yields.
K. Endo, T. Ohkubo, T. Shibata, Org. Lett., 2011,
13, 3368-3371.
