Organic Letters,
Год журнала:
2024,
Номер
26(17), С. 3514 - 3518
Опубликована: Апрель 23, 2024
This
research
presents
an
original
method
for
synthesizing
styrylfurans
using
N-heterocyclic
carbenes
(NHCs)
and
Brønsted
acid
catalysis.
By
exploiting
2,4-dioxoesters
as
conjugated
1,3-dicarbonyls,
we
have
developed
a
technique
allowing
the
efficient
formation
of
highly
functionalized
with
interesting
photochemical
properties,
through
NHC-catalyzed
cross-benzoin
reaction
followed
by
acid-driven
Paal-Knorr-like
condensation.
approach
permits
integration
various
substituents
on
furan
ring,
preliminary
biological
studies
indicating
potential
fluorescent
dyes.
Nature Communications,
Год журнала:
2021,
Номер
12(1)
Опубликована: Июнь 22, 2021
Abstract
There
have
been
significant
advancements
in
radical
reactions
using
organocatalysts
modern
organic
synthesis.
Recently,
NHC-catalyzed
initiated
by
single
electron
transfer
processes
actively
studied.
However,
the
reported
examples
limited
to
catalysis
mediated
alkyl
radicals.
In
this
article,
NHC
organocatalysis
aryl
radicals
has
achieved.
The
enolate
form
of
Breslow
intermediate
derived
from
an
aldehyde
and
thiazolium-type
presence
a
base
undergoes
iodide,
providing
radical.
catalytically
generated
could
be
exploited
as
arylating
reagent
for
relay-type
arylacylation
styrenes
hydrogen
atom
abstraction
α-amino
C(sp
3
)–H
acylation
secondary
amides.
Chemical Science,
Год журнала:
2021,
Номер
12(23), С. 7973 - 7992
Опубликована: Янв. 1, 2021
Molecular
insights
on
the
formation,
detection,
and
even
isolation
of
Breslow
intermediate,
which
is
most
important
species
in
N-heterocyclic
carbene
(NHC)
catalysis,
as
obtained
from
experimental
computational
studies,
are
presented.
The Chemical Record,
Год журнала:
2022,
Номер
22(8)
Опубликована: Май 13, 2022
Abstract
The
recent
advances
in
the
N‐heterocyclic
carbene
(NHC)‐organocatalyzed
generation
of
azolium
enolate
intermediates
and
their
subsequent
interception
with
electrophiles
are
highlighted.
NHC‐bound
generated
by
addition
NHCs
to
suitably
substituted
aldehydes,
acid
derivatives
or
ketenes.
A
broad
range
coupling
partners
can
intercept
enolates
form
[2+n]
cycloadducts
(n=2,3,4)
various
α‐functionalized
compounds.
enantioselective
synthesis
target
compounds
achieved
use
chiral
NHCs.
Herein,
we
summarized
development
that
occurred
this
subclass
NHC
catalysis.
Chemistry - A European Journal,
Год журнала:
2022,
Номер
29(4)
Опубликована: Окт. 7, 2022
N-Heterocyclic
carbene
(NHC)
catalysis
is
a
by
now
consolidated
organocatalytic
platform
for
number
of
synthetic
(asymmetric)
transformations
via
diverse
reaction
modes/intermediates.
In
addition
to
the
typical
umpolung
processes
involving
acyl
anion/homoenolate
equivalent
species,
implementation
protocols
under
oxidative
conditions
greatly
expands
possibilities
this
methodology.
Oxidative
NHC-catalysis
allows
and
oxygenative
through
specific
manipulations
Breslow-type
species
depending
upon
oxidant
used
(external
or
O
Green Chemistry,
Год журнала:
2023,
Номер
25(10), С. 3909 - 3915
Опубликована: Янв. 1, 2023
Visible
light-induced
highly
efficient
synthesis
of
1,3-disubstituted
bicyclo[1.1.1]pentane
with
mild
conditions,
high
atom
economy,
and
superior
functional
group
tolerance.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(11), С. 2670 - 2679
Опубликована: Янв. 1, 2023
A
general
mechanistic
map
involving
multiple
intermediates
and
pathways
has
been
proposed
systematically
studied
for
NHC-catalyzed
transformation
reactions
of
saturated
carboxylic
anhydrides.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6965 - 6972
Опубликована: Апрель 18, 2024
The
synthesis
of
N–N
axially
chiral
molecules
in
the
enantiopure
form
has
emerged
as
an
interesting
research
topic
primarily
due
to
significance
and
intricacy
synthesizing
these
molecules,
especially
bearing
heterocyclic
motifs.
Herein,
we
disclose
a
method
for
introduction
axial
chirality
along
with
point
center
via
N-heterocyclic
carbene
(NHC)-catalyzed
atroposelective
dihydropyridinone-containing
indoles
pyrroles.
reaction
follows
(3
+
3)
annulation
approach
by
interception
indole/pyrrole-derived
enamines
α,β-unsaturated
aldehydes
under
oxidative
NHC
catalysis
proceeding
acylazoliums.
indoles/pyrroles
were
formed
mild
conditions
broad
scope
high
selectivity.
In
addition,
preliminary
DFT
studies
rotational
barrier
products
performed.
Organic Letters,
Год журнала:
2022,
Номер
24(29), С. 5456 - 5461
Опубликована: Июль 20, 2022
Chiral
NHC-catalyzed
kinetic
resolution
of
N-aryl
aminomaleimides
allowing
the
synthesis
C-N
axially
chiral
via
remote
chirality
control
is
presented.
The
catalytically
generated
α,β-unsaturated
acylazoliums
from
2-bromoenals
underwent
selective
[3
+
3]
annulation
with
one
enantiomers
maleimide
to
furnish
fused-dihydropyridinone
(bearing
axial/central
chirality,
up
6:1
dr,
>99:1
er)
leaving
enantioenriched
opposite
enantiomer
(up
er).
Studies
on
bond
rotation
barrier
and
dependence
temperature
are
also
provided.
ACS Catalysis,
Год журнала:
2022,
Номер
12(18), С. 11129 - 11136
Опубликована: Авг. 30, 2022
Herein,
we
report
visible
light
and
N-heterocyclic
carbene
(NHC)
jointly
promoted
multicomponent
transfer
reactions.
Under
the
optimized
reaction
conditions,
two
kinds
of
important
hydroxamic
acid
esters
were
obtained
in
good
yields
depending
on
media
used.
The
key
to
this
success
was
driven
by
blue
light-promoted
generation
free
species
fast
situ
formation
under
NHC-catalyzed
conditions.
mild
excellent
functional
group
tolerance,
useful
synthetic
transformations,
successful
modification
natural
products
drug
molecules
proved
utility
practicality
method.
