Redox-Paired Reductive Heck Reaction and Oxidative Esterification Catalyzed by Mesoionic Carbenes
Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7419 - 7424
Опубликована: Авг. 22, 2024
Paring
a
reductive
reaction
and
an
oxidative
in
one
could
be
immensely
important
achieving
atom
economic
environmental
advantages.
Herein,
we
report
simple
protocol
that
combines
two
such
Heck
reactions
esterification
by
using
mesoionic
carbenes
as
catalysts
to
synthesize
multiple
valuable
products
under
mild
conditions.
Язык: Английский
NHC/Pd Synergistically Catalyzed Direct Aerobic Oxidative Allylic Esterification of Aldehydes
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 21, 2025
N-Heterocyclic
carbene
(NHC)-mediated
aerobic
oxidation
of
aldehydes
has
gained
interest
in
recent
years.
However,
its
application
NHC/Pd
synergistic
catalysis
been
unexplored.
We
have
developed
a
strategy
to
synthesize
allylic
esters
directly
from
and
Morita-Baylis-Hillman
(MBH)
carbonates
using
(cooperative)
under
conditions.
This
transformation
gives
access
the
selective
formation
multifunctionalized
E-alkenes
by
β-attack
on
MBH
carbonates.
catalytic
system
also
allows
use
water
as
cosolvent
air
sole
green
oxidant.
Язык: Английский
Redox Active N-Heterocyclic Carbenes in Oxidative NHC Catalysis
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3114 - 3118
Опубликована: Март 29, 2024
An
N-heterocyclic
carbene
(NHC)
covalently
linked
to
a
quinone
introduces
novel
avenue
for
internal
oxidations
within
oxidative
NHC
catalysis.
The
deployment
of
this
hybrid
class
promotes
intramolecular
electronic
flow
in
the
oxidation
Breslow
intermediate
acyl
azolium.
use
redox
active
as
catalyst
is
facilitated
by
employing
aerobic
regeneration,
yielding
carboxylic
esters
with
efficiencies
≤99%,
while
generating
water
sole
byproduct.
Язык: Английский
An overview on generation and general properties of N-heterocyclic carbenes: Applications of 1,2,4-triazolium carbenes as metal free organocatalysts
Arabian Journal of Chemistry,
Год журнала:
2023,
Номер
17(2), С. 105527 - 105527
Опубликована: Дек. 16, 2023
N-Heterocyclic
carbenes
(NHCs)
have
been
widely
explored
in
the
areas
of
catalysis,
organometallic
and
medicinal
chemistry.
In
particular,
NHCs
catalyze
formation
C-C
C-heteroatom
bounds
with
high
regioselectivity
stereoselectivity
through
umpolung
non-umpolung
processes
for
unconventional
access
to
create
a
vast
scope
heterocycle
molecules,
including
β-lactones,
tetrahydroquinolines
pyrroloquinoles.
Here
we
summarized
generation
general
properties
NHC
important
NHC-catalyzed
reactions,
which
typically
involve
species
such
as
Breslow
intermediates,
homoenolates,
enolates
α,
β-unsaturated
acyl
azoliums,
among
others.
Examples
aerobic
oxidative/oxygenative
carbene
specifically
highlighting
reactions
involving
oxygen
strategies
employed
activation
NHC-catalytic
are
discussed
detail.
The
catalytic
use
has
one
most
powerful
tools
chemist's
arsenal,
applications
commercially
protocols.
Given
this
context,
relevance
N-heterocyclic
chemistry
is
described
review.
Язык: Английский
One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation reaction
Chemical Communications,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
Herein,
we
have
described
a
novel
organocatalytic
approach
to
access
biologically
important
dihydropyridin-2-ones
in
one-pot
way
with
generally
high
yields
(up
99%)
and
excellent
enantioselectivities
99%
ee).
This
reaction
proceeded
Язык: Английский
Expanded scope of chitin-derived nitrogen scaffolds enabled by the 3-acetamido-5-furfurylaldehyde (3A5F) platform
Sustainable Chemistry and Pharmacy,
Год журнала:
2024,
Номер
42, С. 101838 - 101838
Опубликована: Ноя. 9, 2024
Язык: Английский
Unveiling the Hidden Reactivity in the N-Heterocyclic Carbene-Catalyzed Aerobic Oxidation of Aldehydes: Unlocking Its Powerful Catalytic Performance
Chenrui Fan,
Xu Zhao,
Reveendra Gopireddy
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 2, 2024
An
innovative
solution
that
overcomes
the
long-standing
inherently
low
efficiency
in
N-heterocyclic
carbene-catalyzed
aerobic
oxidation
of
aldehydes
is
reported.
This
included
design
and
synthesis
a
novel
polymerized
catalyst
utilization
flow
reactor.
The
unprecedentedly
high
achieved
via
this
protocol
makes
it
synthetically
applicable.
A
total
turnover
number
(TON)
26,300
was
based
on
recycling
experiments
(runs).
highest
TON
single
run
could
be
up
to
2475
with
frequency
(TOF)
208
h–1,
far
superior
its
traditional
counterpart,
which
typical
ranges
from
20
100
TOF
less
than
10
h–1.
has
been
recycled
over
50
times
still
fully
active.
success
attributed
discovery
hidden
reactivity,
observed
for
first
time
as
an
autoacceleration
reaction
rate
during
kinetic
investigations.
research
also
provided
concrete
evidence
supporting
conclusion
radical
intermediates
played
crucial
roles
catalytic
cycle
by
having
determinative
impact
overall
rate.
Язык: Английский