Chemistry - An Asian Journal,
Journal Year:
2023,
Volume and Issue:
18(18)
Published: Aug. 7, 2023
Abstract
Application
of
bioisostere
plays
an
important
role
in
drug
discovery.
α‐Aminoboronic
acid
is
the
familiar
α‐amino
acid.
Developing
reactions
for
synthesis
a
wide
variety
α‐aminoboronic
one
task
synthetic
chemistry.
Herein,
we
report
development
nucleophilic
C
‐borylation
chemistry
N
‐arylimines
catalyzed
by
nickel.
The
reaction
proceeds
through
insertion
borylnickel
species
into
C=N
bond
to
afford
corresponding
α‐aminoboronate,
which
was
isolated
as
acetamide
after
trapping
with
acetic
anhydride.
‐Benzyl
imine
also
tolerated
developed
reaction.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 26, 2024
Abstract
The
copper‐catalyzed
azide
alkyne
[3+2]‐cycloaddition
(CuAAC)
reaction
of
organoboranes
represents
an
attractive
area
research
within
the
field
click
chemistry,
with
diverse
applications
in
organic
synthesis,
medicinal
or
materials
science.
Despite
potential
issues
caused
by
copper
insertion
into
carbon‐boron
bond,
significant
progress
has
been
made
to
harness
reactivity
organoboron
compounds
CuAAC.
This
review
provides
overview
catalytic
methods
reported
for
CuAAC
various
organoboranes,
discussing
stability
boron
group
and
highlighting
recent
advancements
this
area.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(22), P. 4038 - 4043
Published: May 25, 2023
α-Boryl
carbonyl
species
and
α-boryl
amino
compounds
are
valuable
important
frameworks
in
organic
synthesis.
However,
the
strategies
that
could
merge
two
scaffolds
into
one
compound,
named
1,1-carbonyl
alkyl
boron,
elusive
underdeveloped.
Herein,
we
present
an
efficient
method
address
this
gap
produce
borons
from
readily
accessible
indoles
via
oxidation
by
m-CPBA
or
oxone.
This
reaction
features
operational
simplicity,
divergent
synthesis,
broad
substrate
scope,
products.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(7), P. 1099 - 1103
Published: Feb. 15, 2023
α-Boryl
ketones
are
traditionally
challenging
targets
in
organic
synthesis.
Reported
herein
is
a
mild
and
metal-free
synthesis
of
α-boryl
via
the
hydration
or
oxidation
N-methyliminodiacetyl
boronate
(B(MIDA))-decorated
alkynes.
A
new
system
comprised
AcCl
H2O
HFIP
allows
arylethynyl
B(MIDA)s
at
room
temperature
with
decent
functional
group
tolerance.
An
oxidative
carbon
deletion
process
propargylic
also
developed
for
aliphatic
ketones.
intriguing
β-boron
effect
was
observed
to
account
unique
site-
chemoselectivities.
The
application
products
borylated
heterocycles
demonstrated.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(13), P. 4989 - 4995
Published: Jan. 1, 2024
Herein,
we
report
the
potential
utility
of
1,3-enyne
MIDA
boronates
to
access
diverse
gem
-difluoro
via
novel
1,2-alkyne
shift,
various
furan-based
BCMs
5-
endo-dig
cyclization
and
iterative
coupling
partners
hydroboration
diboration
reaction.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
89(1), P. 27 - 33
Published: Dec. 14, 2023
A
practical
and
efficient
synthesis
of
aryl
esters
was
developed
through
metal-free
oxidation.
This
reaction
employs
stable
readily
available
acyl
or
sulfonyl
chlorides
arylboronic
acids
as
the
starting
materials
proceeds
under
mild
conditions
without
additional
precious
metal
catalysts.
new
strategy
exhibits
broad
substrate
tolerance
operational
simplicity
gives
diverse
in
moderate
to
high
yields.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8326 - 8333
Published: May 31, 2024
Here,
we
present
a
straightforward
α-trans-selective
hydroboration
of
alkynyl
sulfones
with
NHC–boranes
without
the
need
for
catalyst.
This
reaction
is
compatible
wide
range
substrates
efficiently
producing
structurally
diverse
α-borylated
vinyl
in
satisfactory
yields.
The
hydride
transfer
from
NHC–borane
2a
to
triflone
1b
studied
by
density
functional
theory
(DFT)
calculations
trans-hydroboration.
Moreover,
regiodivergent
deuterated
semihydrogenation
triflones
has
also
been
developed
using
D2O
as
deuterium
source.
A
variety
diversity-oriented
D-containing
were
prepared
good
excellent
yields
incorporation
ratios.
Synthetic
manipulations
products
are
achieved
conversion
into
valuable
molecules,
indicating
utility
this
protocol.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 21, 2024
Abstract
We
demonstrated
that
the
combination
of
a
Pd(0)
catalyst
and
water‐soluble
TPPMS
ligand
has
high
activity
for
direct
arylation
readily
available
allylic
alcohols
in
Tsuji–Trost
type
cross‐coupling.
Various
organoboron
reagents
can
be
applied,
enabling
rapid
access
to
corresponding
arylated
products
with
wide
range
functional
group
tolerance.
Kinetic
studies
revealed
first‐order
rate
dependence
alcohol,
boronic
acid,
CsF
Pd(0)/TPPMS
concentrations.
A
Hammett
study
found
slightly
positive
ρ
value
0.79,
suggesting
partial
negative
charge
is
generated
on
aromatic
ring
aryl
boronate
rate‐determining
transmetalation
step.
Based
several
control
experiments,
we
concluded
employing
would
proceed
via
oxo‐palladium
mechanism.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(20), P. 5985 - 6003
Published: Jan. 1, 2024
This
review
summarizes
recent
advances
in
alkynyl
trifluoroborate
chemistry,
emphasizing
their
unique
reactivity
and
stability
organic
synthesis
biological
applications
under
transition
metal
catalyst-free
conditions.
