Silver‐Catalyzed Decarboxylative Coupling of Oxamic Acids with Styrenes to Synthesize E‐Cinnamamides: A Distinguish Reaction Pathway
ChemistryOpen,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 29, 2025
Abstract
A
silver‐catalyzed
decarboxylative
coupling
of
oxamic
acids
with
styrenes
has
been
developed
to
produce
E
‐cinnamamides.
Oxamic
act
as
efficient
precursors
for
carbamoy
radicals.
Based
on
the
mechanistic
experiments
and
intermediate
analysis,
proposed
mechanism
involves
radical
addition
styrenes,
followed
by
oxidation
solvent
participation,
ultimately
leading
formation
cinnamamides
which
is
different
from
reported
cases.
Язык: Английский
Facile Synthesis of Carbamoyl Fluorides via N-Carbamoylimidazole Activation
ACS Omega,
Год журнала:
2025,
Номер
10(7), С. 6908 - 6917
Опубликована: Фев. 14, 2025
The
untapped
potential
of
carbamoyl
fluorides
for
various
chemico/biological
applications
is
hampered
by
the
scarcity
straightforward
and
benign
methods
their
synthesis.
In
this
report,
we
disclose
a
novel
mild
three-step
procedure
that
avoids
exotic,
corrosive,
highly
toxic
reagents.
Briefly,
commercially
available
secondary
amines
are
carbamoylated
with
1,1′-carbonyldiimidazole,
followed
alkylation
to
improve
nucleofugality,
exchange
inorganic
KF.
This
works
on
gram
scale
without
chromatographic
purification.
It
however
limited
basic,
sterically
unhindered
alkylation-prone
functional
groups.
Язык: Английский
eFluorination for the Rapid Synthesis of Fluorothioformates from Oxalic Acid Monothioesters
Feba Thomas Pulikkottil,
Marco Galzignato,
Jérémy Saiter
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
An
efficient
and
practical
electrochemical
method
for
synthesizing
fluorothioformate
derivatives,
an
underexplored
functional
group,
is
reported.
The
strategy
based
on
the
anodic
decarboxylation
of
oxalic
acid
monothioesters,
which
rapidly
generates
highly
reactive
alkyl
(oxomethylidene)sulfonium
intermediates.
These
intermediates
are
effectively
trapped
by
inexpensive
commercially
available
triethylamine
trihydrofluoride
(Et3N·3HF),
acts
as
both
a
nucleophilic
fluoride
source
supporting
electrolyte,
leading
to
formation
desired
fluorothioformates.
This
methodology
enables
rapid
scalable
synthesis
enabling
their
broader
exploration
in
organic
chemistry.
In
particular,
these
compounds
can
be
readily
selectively
converted
S-thiocarbamates
urea
derivatives
one-pot
process
through
reactions
with
amines,
demonstrating
synthetic
utility.
scalability
this
fluorination
was
validated,
showing
no
loss
yield.
Cyclic
voltammetry
studies
were
carried
out
shed
some
light
mechanism
novel
transformations.
Язык: Английский
B12‐Catalyzed Carbonylation of Carbon Tetrahalides: Using a Broad Range of Visible Light to Access Diverse Carbonyl Compounds
Chemistry - A European Journal,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 1, 2024
Abstract
Visible‐light‐driven
organic
synthesis
is
a
green
and
sustainable
method
for
producing
fine
chemicals
highly
desirable
at
both
laboratory
industrial
scales.
In
this
study,
we
developed
broad‐range
(including
the
red
region)
visible‐light‐driven
carbonylation
of
CCl
4
,
CBr
3
F
with
nucleophiles,
such
as
amines
alcohols,
using
B
12
−Mg
2+
/TiO
2
hybrid
catalyst.
Carbonyl
molecules
ureas,
carbamates,
carbonate
esters,
carbamoyl
fluorides
were
synthesized
high
selectivity
efficiency
under
mild
conditions.
Diffuse
reflectance
UV‐vis
spectroscopy,
femtosecond
time‐resolved
diffuse
density
functional
theory
calculations
revealed
reaction
mechanism
combination
S
N
single‐electron
transfer.
This
rare
example
low‐energy,
red‐light‐driven
photocatalysis,
which
has
been
desired
in
recent
years.
We
believe
that
study
provides
general
platform
to
access
diverse
carbonyl
could
promote
photocatalytic
reactions
on
pilot
scale.
Язык: Английский