Categories: C-B Bond Formation > Synthesis of potassium trifluoroborates >
Synthesis of alkyltrifluoroborates
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Recent Literature
An operationally simple decarboxylative borylation reaction of readily available
aliphatic acid derivatives under additive-free visible-light photoredox
conditions provides primary and secondary alkyl boronates or tetrafluoroborates
with various functional groups. A catalytic cycle involving alkyl radical
reaction with base-activated diboron species has been proposed.
D. Hu, L. Wang, P. Li, Org. Lett.,
2017, 19, 2770-2773.
A new synthetic method for the preparation of potassium
organotrifluoroborates through nucleophilic substitution of potassium bromo-
and iodomethyltrifluoroborates is described. Potassium
halomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi
with dibromo- and diiodomethane, respectively, in the presence of trialkyl
borates, followed by treatment with KHF2.
G. A. Molander, J. Ham, Org. Lett.,
2006,
8, 2031-2034.
Activated pyridine borane complexes (Py·BH2X) are capable of
hydroborating alkenes at room temperature. An unusual hydroboration
mechanism is discussed. Hydroboration of alkynes with Py·BH2I
selectively affords the monoadducts. The preparation of synthetically useful
potassium alkyltrifluoroborate salts is described.
J. M. Clay, E. Vedejs, J. Am. Chem. Soc.,
2005,
127, 5766-5767.
An oxa-Matteson reaction enables sequential oxygen and carbenoid insertions
into diverse alkyl- and arylboronates to provide a wide range of
boron-substituted ethers. The utilities of this method are demonstrated in the
the asymmetric synthesis of an acetyl-CoA-carboxylase inhibitor, and the
programmable construction of polyethers.
Q. Xi, G. Dong, J. Am. Chem. Soc.,
2022, 144, 8498-8503.
A copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with
tetrahydroxydiborane allows direct, efficient access to boronic acids and their
derivatives. Various α,β-unsaturated amides, ketones and esters are converted to
the corresponding β-trifluoroborato compounds in good to excellent yields.
G. A. Molander, S. A. McKee, Org. Lett., 2011,
13, 4648-4687.
Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were
prepared in good yields from the corresponding unsaturated carbonyl compounds.
They are effective coupling partners in the Suzuki-Miyaura reaction with various
electrophiles including electron-rich and electron-poor aryl bromides and
-chlorides.
G. A. Molander, D. E. Petrillo, Org. Lett., 2008,
10, 1795-1798.
Related:
A new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of potassium bromo- and iodomethyltrifluoroborates is described. Potassium halomethyltrifluoroborates have been prepared via in situ reaction of
n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF2.
G. A. Molander, J. Ham, Org. Lett.,
2006,
8, 2031-2034.
In a one-step synthesis of aliphatic potassium acyltrifluoroborates (KATs)
from organocuprates, organolithium and organomagnesium reagents were readily
transmetalated onto Cu(I) and coupled with a KAT-forming reagent. The protocol
is suitable for primary, secondary and tertiary alkyl substrates.
S. M. Liu, D. Wu, J. W. Bode, Org. Lett.,
2018, 20, 2378-2381.
The cis-dihydroxylation of olefin-containing potassium alkyl- and aryltrifluoroborates proceeds readily in moderate to excellent yields. The resulting diols are efficient coupling partners in Suzuki-Miyaura-type reactions with both alkenyl and aryl bromides.
G. A. Molander, R. Figueroa, Org. Lett., 2006, 8, 75-78.