Helvetica Chimica Acta,
Journal Year:
2023,
Volume and Issue:
106(11)
Published: Sept. 28, 2023
Abstract
The
synthesis
of
monocarborane
sulfonamides
is
reported.
methodology
relies
on
coupling
the
anionic
{CB
11
}
boron
cluster
to
sulfonyl
azides.
Under
rhodium
catalysis
and
with
assistance
a
pyridine
or
pyrimidine
directing
group
at
C1
position,
undergoes
B−H
activation.
Conditions
have
been
identified
that
lead
B2‐selective
mono‐sulfonamidation
concomitant
loss
N
2
.
protocol
requires
no
additional
ligand,
oxidant
base
enables
B−N
bond
formation
various
azide
inputs.
new
products
possess
structure
[1‐(heteroaryl)‐2‐(NHSO
Ar)−CB
H
10
]
−
fully
characterized
by
NMR
spectroscopy
mass
spectrometry.
In
addition,
three
solid
state
structures
confirm
particular
B2
substitution
pattern.
Furthermore,
stoichiometric
reaction
pyridinyl
precursor
Rh(III)
affords
cyclometalated
complex
direct
B−Rh
has
also
X‐ray
crystallography.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(24), P. 4174 - 4188
Published: Dec. 1, 2022
Abstract
Carboranes,
a
three‐dimensional
class
of
carbon‐boron
molecular
clusters
with
remarkable
electronic,
physical,
chemical
characteristics,
have
proved
as
useful
building
blocks
in
boron
neutron
capture
therapy
agents,
supramolecular
design,
optoelectronics,
nanomaterials
and
organometallic/coordination
chemistry.
Thus,
various
organic
modifications
the
B−H
C−H
functionalities
carboranes
been
developed.
These
methods
great
success
utilize
directing
groups,
such
carboxylic
acids,
to
achieve
selective
functionalization
carboranes.
The
carboxyl
group
can
be
easily
introduced
then
removed
after
reactions.
On
other
hand,
assisted
by
highly
regioselective
electrophilic
attack
at
electron‐rich
positions
B(4)
B(5)
cage
generates
five‐membered
metallacyclic
intermediates,
which
undergo
further
transformation.
In
this
review,
we
show
that
transition
metal‐catalyzed
decarboxylation
cross
coupling
reactions
offer
an
opportunity
for
direct
activation
magnified
image
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 11, 2024
Abstract
Carboranes
are
a
type
of
molecular
clusters
consisting
carbon,
hydrogen,
and
boron
atoms.
They
possess
unique
characteristics,
such
as
three-dimensional
aromaticity,
icosahedral
geometry,
robustness.
Functionalized
carboranes
have
been
utilized
in
various
fields,
including
medicine,
materials,
organometallic/coordination
chemistry.
In
this
context,
selective
functionalization
o-carboranes
has
received
tremendous
attention,
specifically
the
regio-
enantioselective
modification
ten
chemically
similar
BH
vertices
within
carborane
cage.
recent
years,
significant
progress
made
catalytic
vertex-specific
functionalization,
well
achieving
cage
BH.
This
review
provides
an
overview
advancements
research
field.
1
Introduction
2
Carboxy-Assisted
Functionalization
2.1
Formation
B–C
Bonds
2.2
B–N
2.3
B–O
2.4
B–X
2.5
Consecutive
B–Y
(Y
=
N,
O)
3
N-Based
Directing-Group-Assisted
B–H
3.1
Acylamino
Directing
Group
3.2
Amide
3.3
Pyridyl
3.4
Imine
4
Phosphinyl-Assisted
Cage
5
Bidentate-Directing-Group-Assisted
6
Other
7
Conclusions
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(44), P. 8794 - 8812
Published: Jan. 1, 2023
Modern
times
have
witnessed
an
uprise
in
the
synthesis
and
derivatization
of
nitrogen-containing
fused
heterocycles.
Amination
reactions
involving
nitrene
chemistry
always
been
most
convenient
choice
for
incorporation
a
nitrogen
atom
molecule.
The
utilization
open
species
harnesses
harsh
conditions.
Hence,
transition
metal-catalyzed
C-H
amination
using
aminating
agents
attractive
choice.
Electrophilic
are
well
exploited
due
to
their
desirable
reaction
Out
all,
anthranils
paved
way
forward
utility
simultaneously
forming
two
new
functional
groups
(amine
carbonyl).
follows
metal-nitrenoid
pathway.
Often,
has
followed
by
Lewis
acid
or
metal-mediated
intramolecular
cyclization
directly
produce
This
review
broadly
demonstrates
as
agent
reactions.
focus
given
scope,
limitations,
mechanistic
understanding
such
electrophilic
agent,
anthranil,
with
metals.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(32), P. 5989 - 5994
Published: Aug. 4, 2023
Iridium(III)-catalyzed
regioselective
B(4)-H
amination
is
developed
from
the
reaction
of
o-carborane
acids
with
sulfilimines
without
any
oxidants
under
mild
conditions,
which
leads
to
a
wide
range
aminated
o-carboranes
in
good
yields
broad
substrate
scope.
Moreover,
selective
B(3,6)-diamination
acid
was
achieved.
The
present
attractive
practical
point
view
because
dibenzothiophene
quantitatively
recovered
and
reused.
Dalton Transactions,
Journal Year:
2023,
Volume and Issue:
52(10), P. 2933 - 2936
Published: Jan. 1, 2023
An
iridium-catalyzed
selective
amination
of
B(4)-H
via
dehydrogenative
cross-coupling
B-H/N-H
bonds
for
the
synthesis
o-carborane-fused
indolines
has
been
developed
first
time.
Various
types
unprecedented
have
synthesized,
which
would
be
potential
candidates
applications
in
drug
discovery,
pharmaceutical
chemistry
and
functional
materials.
This
work
offers
a
valuable
reference
designing
heterocycles.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
12(3)
Published: Dec. 21, 2022
Abstract
A
ruthenium‐catalyzed
selective
B4
amidation
of
o
‐carboranes
with
a
variety
alkyl‐,
aryl‐,
and
heteroaryl‐substituted
dioxazolones
is
developed
by
carboxylic
acid‐assisted
B(4)‐H
bond
activation
in
‐carborane
acids,
affording
multitude
(4)‐amidated
good
yields
the
evolution
carbon
dioxide.
In
addition,
two‐fold
decarboxylative
reaction
cage
was
accomplished.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(20), P. 4036 - 4040
Published: Jan. 1, 2024
An
unprecedented
Ir(
iii
)-catalyzed
C–H
activation/amination/annulation
of
2-phenyloxazoles
with
anthranils
for
the
highly
selective
preparation
acridone
derivatives
in
one-pot
under
controlled
conditions
is
reported.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(60), P. 7749 - 7752
Published: Jan. 1, 2024
An
efficient
approach
for
the
synthesis
of
pyridoquinazolinones
in
presence
triflic
anhydride
utilizing
anthranil
and
2-chloropyridines
as
starting
materials
has
been
developed.
